100 named reactions with examples of total syntheses which utilized these reactions, with reaction conditions. with included references for each syntheses.

1. Assignment
In
Hundred named Reactions used in Organic Syntheses
Submitted by
Roshen Reji Idiculla
ID MS14/11
Submitted to
Prof. Dr. Ibnu Saud
SI.
NO
NAME REACTION REAGENTS
CONDITIONS
Yi
eld
1. Robinson annulation Et3N
0 °C to RT, 7 h
EWG activated
π systems
78 Total Synthesis of (-)-Chromodorolide B J. Am. Chem. Soc., 2016, 138 (7), pp 2186–2189
substrate product
Michael addition (attack of
stabilized carbon nucleophiles on
EWG activated π systems) of
prochiral 3 with enone 4 (α,
unsaturated ketone). The generation
of C nucleophiles (Michael donor)
require use of non-nucleophilic
bases.
Then Intramolecular aldol reaction
Base catalyzed dehydration yielding
substituted cyclohexenone
2 Cu-Al Ox-mediated enone allylic
hydroxylation
Cu-Al
ether
85 This was used in total synthesis of Pavidolide B
substrate product

2. 3
.
Mitsunobu reaction 90
substrate product
Converts an alcohol into a variety of
functional groups.
an inversion of stereochemistry
4 meyer-schuster-rearrangement 82 Total synthesis of (-)-enigmazole A. doi 10.1002/anie.201801561 , gold-catalyzed Meyer–Schuster-
type rearrangement of propargylic benzoate.substrate product
secondary and
tertiary
propargyl
alcohols
α,β-unsaturated
ketones
acid-catalyzed rearrangement of
secondary and tertiary propargyl
alcohols to α,β-unsaturated ketones
5. Evans–Tishchenko reaction 90 This is used in Total synthesis of (-)-enigmazole A. doi 10.1002/anie.201801561
substrate product
β-hydroxy
ketones
1,3-anti diol
monoesters
diastereoselective reduction of β-
hydroxy ketones to the
corresponding 1,3-anti diol
monoesters
Lewis acid samarium iodide,
chelates aldehyde and ketone
oxygen in a Zimmweman taxler
model, 6-membered transition state.
The aldehyde formyl hydrogen
migrate intramolecularly to anti
diastereoselectivity
6 krapcho-decarboxylation 78 This is used in total synthesis of (+) Aplykurodinone-1 Org. Lett. 2017, 19, 18, 4861-4863
substrate product

3. ester having an
electron-
withdrawing
group in the beta
position
alkane
involves loss of an alkoxycarbonyl
group from ester having an electron-
withdrawing group in the beta
position
7 Lemieux-Johnson oxidation 84 This is used in total synthesis of Magellanine, McGee, P.; Bétournay, G.; Barabé, F.; Barriault,* L.
Angew. Chem. Int. Ed. 2017, 56, 6280-6283substrate product
Olefin two aldehyde or
ketone units
involves oxidative cleavage of a
olefin to form two aldehyde or
ketone units. 1st
step is
dihydroxylation of the alkene by
osmium tetroxide, followed by a
Malaprade reaction to cleave the
diol using periodate
8 Corey–Fuchs alkynylation 78 This is used in Total synthesis of (-)-enigmazole A. doi 10.1002/anie.201801561
substrate product
invovles formation of the 1,1-
dibromoolefins from aldehydes via
phosphine-dibromomethylenes,
which is then converted to to
alkynes , by Buttenberg–Wiechell
rearrangement
9 peterson-olefination This is used in total synthesis of Tetrodotoxin, Maehara, T,; Motoyama, K.; Toma, T.; Yokoshima, S.;
Fukuyama, T Angew. Chem. Int. Ed. 2017, 56, 1549-1552substrate product
α-silyl with
ketones (or
aldehydes)
a β-hydroxysilane
involves formation of a β-
hydroxysilane from α-silyl with
ketones (or aldehydes) which then
eliminates to form alkenes.
10
yamaguchi-esterification 85 This is used in total synthesis of Tetrodotoxin, Maehara, T,; Motoyama, K.; Toma, T.; Yokoshima, S.;
Fukuyama, T Angew. Chem. Int. Ed. 2017, 56, 1549-1552substrate product
aliphatic
carboxylic
acid
mixed anhydride

4. involves formation of mixed
anhydride from aliphatic carboxylic
acid and 2,4,6-trichlorobenzoyl
chloride (TCBC, Yamaguchi
reagent) . this mixed anhydride
which, react with an alcohol in the
presence of stoichiometric amount
of DMAP, giving desired ester.
11 finkelstein-reaction 74 This is used in Total synthesis of Sterpurenone, , Sahu, R.; Singh, V. J. Org. Chem. 2017, 82, 6268-
6278substrate product
involves SN2 reaction (Substitution
Nucleophilic Bimolecular reaction)
that involves the exchange of one
halogen atom as nucleophile.
12 pauson-khand-reaction 90 this is used in Total synthesis of Ryanodol, Chuang, K. V.; Xu, C.; Reisman, S. E. Science 2016, 353,
912.substrate product
involves [2+2+1] cycloaddition
between an alkyne, an alkene and
carbon monoxide to form a α,β-
cyclopentenone.
13 Michaelis–Arbuzov reaction 94 This is used in total synthesis of Rubriflordilactone B, Yang, P.; Yao, M.; Li, J.; Li, Y.; Li, A. Angew.
Chem. Int. Ed. 2016, 55, 6964.substrate product
(also called the Arbuzov reaction)
involves pentavalent phosphorus
species like phosphonates from
trivalent phosphorus ester with an
alkyl halide
14 Dieckmann condensation
NaBH4
91 This is used in total synthesis of Rubriflordilactone B, Yang, P.; Yao, M.; Li, J.; Li, Y.; Li, A. Angew.
Chem. Int. Ed. 2016, 55, 6964.substrate product
involves intramolecular reaction of
diesters with base to give β-keto
esters
15 fischer-indole-synthesis 75 This is used in Synthesis of Spiroindimicin B. Chem. Commun. 2016, 52, 800.
Substrate product

5. involves formation of a indole from
a (substituted) phenylhydrazine and
an aldehyde or ketone under acidic
conditions
16 wohl-ziegler-reaction 95
This is used in Synthesis of Spiroindimicin B. Chem. Commun. 2016, 52, 800.substrate product
involves formation of allylic or
benzylic bromides using an N-
bromosuccinimide and a radical
initiator Then Intramolecular aldol
reaction
Base catalyzed dehydration yielding
substituted cyclohexenone
17 Barton–Zard_reaction 88
This is used in Synthesis of Spiroindimicin B. Chem. Commun. 2016, 52, 800.substrate product
involves formation of pyrrole
derivatives via the reaction of a
nitroalkene with an α-
isocyanoacetate under basic
conditions.
18 gassman-indole-synthesis 77 This is used in total synthesis of Leuconoxine Chem. Eur. J. 2015, 21, 6355.
substrate product

6. involves formation of substituted
indoles by addition of an aniline and
a ketone bearing a thioether
substituent
19 parikh-doering-oxidation 89
This is used in total synthesis of Leuconoxine, Chem. Eur. J. 2015, 21, 6355.substrate product
oxidation involves oxidation of
primary and secondary alcohols into
aldehydes and ketones. Using
dimethyl sulfoxide (DMSO) as the
oxidant, activated by the sulfur
trioxide pyridine complex in the
presence of triethylamine base.
20 Darzens reaction 96
This is used in Total synthesis of Rubrobramide, Mizutani, S.; Komori, K.; Taniguchi, T.; Monde, K.;
Kuramochi, K.; Tsubaki, K. Angew. Chem. Int. Ed. 2016, 55, 9553-9556.
substrate product
(also known as the Darzens
condensation or glycidic ester
condensation) involves formation of
α,β-epoxy ester from ketone or
aldehyde with an α-haloester in the
presence of a base.
21 rubottom-oxidation 76 This is used in Synthesis of Kinamycin F. J. Am. Chem. Soc. 2010, 132, 2540.
substrate product
involves formation of α-hydroxy
carbonyl product from silyl enol
ethers and peroxyacids
22 ley-griffith-oxidation 91 This is used in Synthesis of Caribenol A, J. Am. Chem. Soc. 2010, 132, 13608.
substrate product

7. Involves selective oxidation of
alcohols to aldehydes or ketones
23 pinnick-lindgren-oxidation 89 this is used in Total synthesis of Vincorine, Horning, B. D.; MacMillan, D. W. C. J. Am.Chem. Soc.
2013, 135, 6442-6445.substrate Product
involves oxidation of aldehydes into
carboxylic acids using sodium
chlorite (NaClO2) under mild acidic
conditions
24 shapiro-reaction 85 This is used in Total synthesis of Artemisinin, Zhu, C.; Cook, S. P. J. Am. Chem. Soc. 2012, 134,
13577-13579substrate product
involves conversion of ketone or
aldehyde to an alkene through an
intermediate hydrazone in the
presence of 2 equivalents of
organolithium reagent
25 julia-kociensky-olefination 83 This is used in Total synthesis of Apiosporic Acid, Gärtner, M.; Kossler, D.; Pflästerer, D.; Helmchen,
G. J. Org. Chem, 2012, 77, 4491-4495substrate product
involves reaction of phenyl sulfones
with aldehydes (or ketones) to give
E alkenes
26 . saegusa-ito-oxidation 95 This is used in Total synthesis of Cycloclavine, Petronijevic, F. R.; Wipf, P. J. Am. Chem. Soc. 2011,
133, 7704–77079substrate product

8. involves formation of α-β
unsaturated carbonyl compounds,
from silyl enol ether and
palladium(II) acetate
27 lemieux-johnson-oxidation 89 This is used in Synthesis of Solandelactone E, Angew. Chem. Int. Ed. 2010, 49, 6673
substrate product
involves oxidative cleavage of
olefins to aldehydes or ketones
28 rosenmund-von-braun-reaction 80 this is used in Synthesis of Ammosamide B J. Am. Chem. Soc. 2010, 132, 2528.
substrate product
involves formation of an aryl nitrile
from aryl halide and cuprous
cyanide
29 fischer-esterification 86 this is used in Synthesis of Ammosamide B J. Am. Chem. Soc. 2010, 132, 2528.
substrate product
involves ester formation from
primary, secondary alcohols ,
phenols in acidic medium
30 overman-rearrangement benzene 97 This is used in Synthesis of Aspidofractinine, J. Org. Chem. 2009, 74, 6035.
substrate product
involves Claisen rearrangement of
allylic alcohols to give allylic
trichloroacetamides through an
imidate intermediate

9. 31 curtius-rearrangement 87
This is used in Synthesis of Oseltamivir Angew. Chem. Int. Ed. 2009, 48, 1304.
substrate product
involves thermal decomposition of
an acyl azide to an isocyanate with
loss of nitrogen gas.
32 williamson-ether-synthesis 95 This is used in Synthesis of Glycyrol, Tetrahedron Lett. 2008, 49, 6835.
substrate product
33 henry-reaction 96 This is used in Total synthesis of Nakadomarin A, Jakubec, P.; Cockfield, D. M.; Dixon, D. J. Am.
Chem. Soc. 2009, 131, 16632–16633substrate product
involves formation of β-Nitro
alcohols from nitroalkane and an
aldehyde or ketone in the presence
of a base
34 johnson-claisen-rearrangement 91 This is used in Synthesis of Nupharamine , Synlett 2010, 866.
substrate product

10. involves formation of γ,δ-
unsaturated ester, from allylic
alcohol and orthoester.
35 horner-wadsworth-emmons-reaction 78 This is used in Synthesis of Nupharamine , Synlett 2010, 866.
substrate product
involves formation of E-alkenes
from stabilized phosphonate
carbanions and aldehydes (or
ketones).
36 ramberg-baumlcklund-reaction 84 This is used in Synthesis of Aigialomycin D, J. Org. Chem. 2009, 74, 2271.
substrate product
involves formation of Z alkenes (
weak bases) , or E alkenes (strong
bases) from α-halosulfones
37 marko-lam-deoxygenation 25 This is used in Synthesis of Trifarienol B, Angew. Chem. Int. Ed. 2008, 47, 131.
substrate product
involves conversion of hydroxy
functional group in an organic
compound to a hydrogen atom to
give an alkyl group
38 morita-baylis-hillman-reaction 67 This is used in Synthesis of Grandisine D, Org. Lett. 2009, 11, 1179.
substrate product

11. involves C-C bond formation
between α-position of an activated
alkene and a carbon electrophile
such as an aldehyde using
nucleophilic catalyst, such as a
tertiary amine and phosphine.
39 barton-mccombie-reaction 94
This is used in Synthesis of Grandisine D, Org. Lett. 2009, 11, 1179.substrate product
40 evans-mislow-rearrangement 89 This is used in total Synthesis of Agelastatin A, Org. Lett. 2009, 11, 2687.
substrate product
involves formation of allylic
alcohols from allylic sulfoxides in a
2,3-sigmatropic rearrangement.
41 barton-vinyl-iodide-synthesis 65 this is used in Synthesis of Cortistatin A, J. Am. Chem. Soc. 2008, 130, 7241.
substrate product
involves formation of vinyl iodide
from a hydrazone iodine and a non-
nucleophilic base such as DBU
43 seyferth-gilbert-homologation 55 This is used in Synthesis of Alstonerine, J. Org. Chem. 2003, 68, 8867.
substrate product
involves formation of substituted
alkyne, from aryl ketone (or
aldehyde) with dimethyl
(diazomethyl)phosphonate and
potassium tert-butoxide. .
44 The_Schlosser modification 89 This is used I total Synthesis of Pseudolaric Acid B, J. Am. Chem. Soc. 2007, 129, 14556.
substrate product

12. involves formation of an alkene and
triphenylphosphine oxide from
aldehyde or ketone with an
unstabilised triphenyl phosphonium
ylide. The erythro betaine in Wittig
can be converted to the threo betaine
using phenyllithium at low
temperature, leading to E-alkene.
45 prilezhaev-reaction 98 This is used I total Synthesis of Pseudolaric Acid B, J. Am. Chem. Soc. 2007, 129, 14556.
substrate product
, involves formation of epoxides
from alkene and peroxy acid
46 benzoin-condensation 78 This is used in Synthesis of Kinamycin F, J. Am. Chem. Soc. 2007, 129, 10356.
substrate product
involves 1,2-addition reaction of two
aldehydes catalyzed by nucleophiles
such as a cyanide anion or an N-
heterocyclic carbene (usually
thiazolium salts ) forming an
aromatic acyloin
47 pinner-reaction 60 This is used in Synthesis of Oseltamivir, Org. Lett. 2007, 9, 259.
substrate product
involves formation of imino ester
salt, Pinners salt, from nitrile with an
alcohol.

13. 48 weinreb-ketone-synthesis 52 This is used in Synthesis of Nominine, J. Am. Chem. Soc. 2006, 128, 8734.
substrate product
, involves formation of ketones from
Weinreb–Nahm amide, and
organometallic reagent or carbon
nucleophiles
49 staudinger-reaction 56 This is used in Synthesis of Saxitoxin, J. Am. Chem. Soc. 2003, 125, 2028.
substrate product
involves formation of
triphenylphosphine phenylimide,
which on hydrolysis produces a
phosphine oxide and an amine
50 evans-saksena-reduction 90 This is used in Synthesis of Kinamycin C, J. Am. Chem. Soc. 2006, 128, 14790.
substrate product
involves diastereoselective reduction
of β-hydroxy ketones to the
corresponding anti-dialcohols,
employing the reagent
tetramethylammonium
triacetoxyborohydride
(Me4NHB(OAc)3).
51 kulinkovich reaction 60 This is used in Synthesis of B-Araneosene, J. Am. Chem. Soc. 2005, 127, 13813.
substrate product
involves formation of
cyclopropanols from reaction of
esters with dialkyldialkoxytitanium
reagents.

14. 52 fukuyama-indole-synthesis 52 This is used in Synthesis of Strychnine, J. Am. Chem. Soc. 2004, 126, 10246.
substrate product
involves formation of 2,3-
disubstituted indoles, from benzene
unit with o-isocyano carbon or 2-
alkenylthioanilide using tributyltin
hydride the reducing agent, and
azobisisobutyronitrile (AIBN) as a
radical initiator
53 larock-indole-synthesis 75 This is used in Synthesis of Strychnine, J. Am. Chem. Soc. 2004, 126, 10246.
substrate product
, involves formation of synthesize
indoles from an ortho-iodo aniline
and a disubstituted alkyne, using
heteroannulation reaction and
palladium as a catalyst
54 takai-reaction 79 This is used in Synthesis of Quinine, J. Am. Chem. Soc. 2004, 126, 706.
substrate Product
involves formation of alkene from
an aldehyde with a
diorganochromium compound

15. 55 grieco-dehydration 77 this is used in Synthesis of Quinine, Tetrahedron Lett. 2004, 45, 3783.
substrate Product
involves formation of a terminal
alkene by elimination reaction of an
aliphatic primary alcohol using
selenide
56 wolff-rearrangement 72 . This is used in Synthesis of Pentacycloanammoxic Acid, J. Am. Chem. Soc. 2004, 126, 15664.
substrate product
, involves formation of ketone from
α-diazocarbonyl compound by loss
of dinitrogen with accompanying
1,2-rearrangement
57 schmidt-reaction 86 This is used in Total synthesis of Stenine, Frankowski, K. J.; Golden, J. E.; Zeng, Y.; Lei, Y.; Aubé,
J. J. Am. Chem. Soc. 2008, 130, 6018–6024.substrate product
involves formation of amine
(carboxylic acid) or amide (ketone) ,
from reaction of azide reacts with a
carbonyl group
58 simmons-smith-reaction 75 This is used in Total synthesis of Hirsutene, Jiao, L.; Yuan, C.; Yu, Z.-X. J. Am. Chem. Soc. 2008,
130, 4421.
substrate product
involves formation of cyclopropane
from organozinc carbenoid and an
alkene.
59 nef-reaction 51 this is used in Total synthesis of Tetrodotoxin , Sato, K.; Akai, S.; Shoji, H.; Sugita, N.; Yoshida,
S.; Nagai, Y.; Suzuki, K.; Nakamura, Y.; Kajihara, Y.; Funabashi, M.; Yoshimura, J.; JOC. 2008,
73, 1234
substrate product
involves formation of ketone and
aldehyde from a primary or
secondary nitroalkane
60 liebeskind-srogl-coupling 94 This is used in Synthesis of Sphingosine. Org. Lett. 2007, 9, 2993.

16. substrate product
involves formation of carbon-carbon
bond from thioester and a boronic
acid using a metal catalyst
61 mukaiyama-aldol-addition 58 This is used in Total synthesis of Cryptocarya Diacetate. Boxer, M. B.; Yamamoto, H. J. Am. Chem.
Soc., 2007, 129, 2762-2763substrate product
involves aldol reaction between a
silyl enol ether and an aldehyde or
formate
62 maitland-japp-reaction 60 This is used in Synthesis of Centrolobine. Tetrahedron 2005, 61, 5433.
substrate product
involves two reactions. 1st
reaction
between the ketone and the aldehyde
catalyzed by base the bis Aldol
adduct is formed first. The second
step is a ring-closing reaction when
one hydroxyl group displaces the
other in a nucleophilic substitution
forming an oxo-tetrahydropyran.
63 baeyer-villiger-oxidation 61 . This is used in Synthesis of Reserpine, J. Am. Chem. Soc. 2005, 127, 16255.
substrate product
involves formation of an ester from
a ketone or a lactone from a cyclic
ketone, using peroxyacids or
peroxides as the oxidant

17. 64 fleming-tamao-oxidation 61 This is used in Synthesis of Reserpine, J. Am. Chem. Soc. 2005, 127, 16255.
substrate product
involves oxidation of carbon–silicon
bond to a carbon–oxygen bond with
a peroxy acid or hydrogen peroxide
65 neber-rearrangement 89 This is used in Synthesis of Dragmacidin F, J. Am. Chem. Soc. 2002, 124, 13179.
substrate product
, involves formation of alpha-
aminoketone from ketoxime via a
rearrangement reaction
66 stork danheiser reaction 59 This is used in Total synthesis of Platensimycin, Nicolaou, K. C.; Li, A.; Edmonds, D. J. Angew.
Chem. Int. Ed. 2006, 45, 7086.substrate product
involves reaction of the β alkoxy
ketene with an organometallic
compound followed by acid
treatment to obtain another ketene
reaction, and the position of the
carbonyl group of the newly formed
ketene is the olefinic carbon of the
enol ether in the starting material.
67 wacker-oxidation 95 This is used in Total synthesis of Dichroanone, McFadden, R. M.; Stoltz, B. M. J. Am. Chem. Soc.
2006, 128, 7738substrate product
involves oxidation of alkene to
ketone in the presence of
palladium(II) chloride as the
catalyst.

18. 68 fritsch-buttenberg-wiechell-
rearrangement
91 This is used in Total synthesis of Amphidinolide E, Va, P.; Roush, W. R. J. Am. Chem. Soc. 2006,
128, 15960.
substrate product
involves rearrangmente of 1,1-
diaryl-2,2-dibromo-alkene to alkyne
by reaction with a strong base
69 ullmann-coupling 85 This is used in Total synthesis of Staphacidin, Herzon, S. B.; Myers, A. G J. Am. Chem. Soc. 2005,
127, 5342substrate product
involves coupling reaction between
aryl halides and copper
70 grob-fragmentation
substrate product
involves elimination reaction of a
neutral aliphatic chain into three
fragments: a positive ion a
carbenium, carbonium or acylium
ion, an unsaturated neutral an
alkene, alkyne, or imine and a
negative ion (the "nucleofuge") tosyl
or hydroxyl ion:
71 corey-itsuno-reaction 75 This is used in Synthesis of Panaxytriol, J. Org. Chem. 2003, 68, 4519.
substrate product
also known as the Corey–Bakshi–
Shibata (CBS) reduction involves
formation of chiral, non-racemic
alcohol, from an achiral ketone
72 cadiot-chodkiewics-reaction 63 This is used in Synthesis of Panaxytriol, J. Org. Chem. 2003, 68, 4519.
substrate product

19. involves coupling reaction between
a terminal alkyne and a haloalkyne
catalyzed by a copper(I) salt such as
copper(I) bromide and an amine
base to form 1,3-diyne or di-alkyne.
73 lombardo-methylenation 72 This is used in Synthesis of Tetrodotoxin, J. Am. Chem. Soc. 2003, 125, 11510.
substrate product
involves methylation of unreactive
ketones
74 pechmann-condensation 47 This is used in Synthesis of Aflatoxin B1, J. Am. Chem. Soc. 2003, 125, 3090.
substrate product
synthesis of coumarins, starting
from a phenol and a carboxylic acid
or ester containing a β-carbonyl
group
75 corey-posner-whitesides-house-
reaction
95 this is used in Synthesis of Ingenol, J. Am. Chem. Soc. 2003, 125, 1498.
Substrate product
involves formation of a new alkane
from lithium diorganylcuprate
(R2CuLi) with an organyl
(pseudo)halide (R'X) .
76 Ritter reaction 73
this is used in enantiospecific synthesis of Jiadifenolide, http://dx.doi.org/10.1002/anie.201402335
substrate product

20. ,involves the acid-induced
nucleophilic addition of a nitrile to a
carbenium ion, followed by
hydrolysis to the corresponding
amide
77 blaise-reaction 67 This is used in Synthesis of (−)-Lasonolide A http//dx.doi.org/10.1021/ja411270d
substrate product
involves formation of β-ketoester
from the reaction of zinc metal with
a α-bromoester and a nitrile
78 marshall-propargylation 65 This is used in Synthesis of Amphidinolide F, http://dx.doi.org/10.1002/anie.201301700
substrate product
propargylation involves C-C
coupling between propargyl
mesylates and aldehydes .
79 Schwartz reaction 79
This is used in Synthesis of Branimycin, http://dx.doi.org/10.1002/chem.201200257
substrate product
, involves reaction of
organozirconium intermediates with
electrophiles iodine, bromine and
acid chlorides to give the
corresponding haloalkanes, and
ketones
80 Kornblum oxidation 76 this is used in synthesis of Deoxy-Penostatin A Snider, B. B.; Liu, T. J. Org. Chem. 2000, 65, 8490-
8498substrate product
involves reaction of a primary halide
with dimethyl sulfoxide (DMSO) to
form an aldehyde.
81 Arndt–Eistert reaction Ag(O2CCF3)2
Ag+ (cat)
88 This is used in synthesis of JuvabioneSoldermann, N.; Velker, J.; Vallet, O.; Stoeckli-Evans, H.;
Neier, R. Helv. Chim. Acta 2000, 83, 2266.substrate product

21. involves conversion of carboxylic
acid to a higher carboxylic acid
homologue
82 Jones oxidation 85 This is used in synthesis of Hispidospermidine, Frontier, A. J.; Raghavan, S.; Danishevsky, S. J. J.
Am. Chem. Soc. 2000, 122, 6151.substrate product
involves oxidation of primary and
secondary alcohols to carboxylic
acids and ketones, respectively
83 vilsmeier-haack-formylation 66 this is used in synthesis of Illudin C, Aungst, R. A.; Chan, C.; Funk, R. L. Org. Lett. 2001, 3, 2611.
substrate product
involves substituted amide with
phosphorus oxychloride and an
electron-rich arene or alkene to
produce an aryl aldehyde or ketone
84 pummerer-rearrangement 88 This is used in synthesis of Solanapyrone:, Hagiwara, H.; Kobayashi, K.; Miya, S.; Hoshi, T.;
Suzuki, T.; Ando, M.; Okamoto, T.; Kobayashi, M.; Yamamoto, I.; Ohtsubo, S.; Kato, M.; Uda, H.J.
Org. Chem. 2002, 67, 5969.
substrate product
involves rearrangement of alkyl
sulfoxide to an α-acyloxy–thioether
(monothioacetal-ester) in the
presence of acetic anhydride.
85 mcmurry-reaction 90 This is used in synthesis of (±)-δ-Araneosene, Hu, T.; Corey, E. J. Org. Lett. 2002, 4, 2441
substrate product
involves coupling of two ketone or
aldehyde groups to an alkene using a
titanium chloride compound such as
titanium(III) chloride and a reducing
agent

22. 86 Stobbe-condensation 98 This is used in synthesis of Acitretin, , Andriamialisoa, Z.; Valla, A.; Cartier, D.; Labia, R. Helv.
Chim. Acta 2002, 85, 2926.substrate product
modification of Claisen
condensation involving dialkyl ester
of carboxylic acid requiring less
strong bases
87 Reformatsky reaction
Zn
66 This is used in synthesis of Waol A, Gao, X.; Nakadai, M.; Snider, B. Org. Lett. 2003, 5, 451
substrate product
involves condensation of aldehydes
or ketones, with α-halo esters, using
a metallic zinc to form β-hydroxy-
esters
88 Corey winter reaction 76 This is used in synthesis of Astellatol. https://doi.org/10.1002/anie.201800167
substrate product
reaction involves Ei mechanism. It
converts vicinal diols to alkenes via
cyclic thionocarboxylates.
89 achmatowicz-reaction 90 This is used in Total Synthesis of Cyclocitrinol. J. Am. Chem. Soc., 2018, 140 (16), pp 5365–5369
substrate Product
involves rearrangement of furan to a
dihydropyran
91 Fukuyama reduction 97 This is used in Synthesis of Divergolide I, J. Am. Chem. Soc. 2018, 140, 8, 2748-2751

23. substrate Product
, involves reduction of a thioester is
to an aldehyde by a silyl hydride in
presence of a catalytic amount of
palladium
92 Shiina esterification 71 This is used in Synthesis of Divergolide I, J. Am. Chem. Soc. 2018, 140, 8, 2748-2751
substrate product
involves formation of carboxylic
esters from nearly equal amounts of
carboxylic acids and alcohols by
using aromatic carboxylic acid
anhydrides as dehydration
condensation agents.
92 Rautenstrauch reaction 80
This is used in Synthesis of (+)‐ and (±)‐Hosieine A, https://doi.org/10.1002/anie.201804076substrate product
involves gold-catalyzed cyclization
reactions using the activation of
alkynes by gold(I) to form
cyclopent-2-enones.
93 Dakin oxidation (or Dakin reaction) 58
This is used in Synthesis of (±)‐Phomoidride D https://doi.org/10.1002/anie.201712369substrate product
involves oxidation of ortho- or para-
hydroxylated phenyl aldehyde (2-
hydroxybenzaldehyde or 4-
hydroxybenzaldehyde) or ketone
with hydrogen peroxide in base to
form a benzenediol and a
carboxylate
94 Riley oxidation 47 This is used in Synthesis of Salimabromide,J. Am. Chem. Soc. 2018, 140, 27, 8444-8447
substrate product

24. involves selenium dioxide-mediated
oxidation of methylene groups
adjacent to carbonyls
95 hunsdiecker-reaction 87 This is used in synthesis of (±)-Aspergilline A, J. Am. Chem. Soc., 2017, 139 (51), pp 18504–18507
substrate product
involves reaction of silver salts of
carboxylic acids with halogen to
produce an organic halide.
96 Chugaev elimination 78
This is used in Synthesis of (±)-lycoricidine J. Org. Chem., 2007, 72, 2570-2582.
substrate product
an example of Ei mechanism ,
similar to ester pyrolysis. It
converts alcohols with 𝛽 H to
alkenes, via xanthate formation
97 friedlaender-synthesis.
BuLi
THF
Then MeOH
84 This is used in synthesis of poly-substituted quinolones, C.-S. Jia, Z. Zhang, S.-J. Tu, G.-W. Wang,
Org. Biomol. Chem., 2006, 4, 104-110.substrate product
Involves formation of quinoline
derivatives from 2-
aminobenzaldehydes with ketones
98 Pfitzner–Moffatt oxidation 78 This is used in Synthesis of 18R-hydroxy-epiallo-yohimbines https://doi.org/10.1016/S0040-
4039(00)00913-8
substrate product

25. 99 arbuzov-reaction. 75 This is used in Synthesis of (−)-Epibatidine ,Org. Lett., 2001, 3 (19), pp 3009–3012
substrate product
form a pentavalent phosphorus
species from a trivalent phosphorus
ester with an alkyl halide
100 (Fleming-) Tamao (-Kumada)
Oxidation
80 This is used in Total Synthesis of Eunicenone A
J. Am. Chem. Soc., 2001, 123 (9), pp 1872–1877substrate product
Oxidation of alkyl fluorosilanes to
the corresponding alcohols.