1. CURRICULUM VITAE
M. SIVAGURU
Senior Research Scientist
Albany Molecular Research Center
Alexandria Knowledge Park, Genome Valley
Turkapally, Shameerpet,
Hyderabad, India
E-mail: sivaguru1980@gmail.com
Mobile: +919791711151
CAREER OBJECTIVES
To be an active participant in Research and Development with new trends of technology
on synthetic organic chemistry and medicinal chemistry, where I can contribute my best
efforts to reach the apex my career.
ACADEMIC RECORDS
Oct. 2008-June 2014 Ph.D Synthetic Organic Chemistry with four years‟ experience in
API industry
Bharathidasan University, Trichirappalli, Tamil Nadu, India
Thesis Title: “Studies on the reactions of diazocarbonyl
compounds: Synthesis and characterization of macrodiolide,
indole, indene and furanone derivatives.”
Defended thesis on 7th
May 2015.
Jun. 2003-May 2005 M. Sc. Organic Chemistry, Department of Organic Chemistry,
University of Madras, Guindy Campus, Chennai 600025, Tamil
Nadu, India.
Project with Prof. R. Raghunathan, University of Madras,
Chennai, Project Title: “Synthesis of novel Spiroheterocycle
through 1,3-dipolar cycloaddition”.
Jul. 1999-May 2002 B. Sc. Chemistry, Tagore Arts and Science College, Pondicherry
University, India.
INDUSTRIAL EXPERIENCES
Jun 2016 to till date working as Senior Research Scientist (Scale up process R
& D) in Albany molecular research center, Hyderabad.

2. Jan 2016 to May 2016 Worked as chemistry subject matter expert in SPi
Technologies, Chennai
Nov. 2014 to Sep 2015 Worked as Research Scientist in Sun Pharmaceuticals
Ltd, Formerly known as Ranbaxy Laboratories, Guragon,
Haryana, India.
Dec. 2006 to Mar. 2008 Worked as a research associate in Cadila
Pharmaceuticals, Bangalore, Karnataka, India.
Jul. 2005 to Nov. 2006 Worked as research executive Cipla Pharmaceuticals,
Bangalore, Karnataka, India.
AWARDS/FELLOWSHIPS
 Awarded Research Fellowship (SRF) by Council for Scientific and Industrial
Research, India (2008-11).
 Awarded Research Fellowship (JRF) by University Grants Commission-
Research Fellow Scheme Meritorious Students, India (2013-14).
 Summer training in chemistry for the pre-final post-graduate Students, during
June-July 2004, Malladi drugs and pharmaceuticals, Eakatuthangal, Chennai-
603102, Tamil Nadu, India.
 Got 2th
rank in M. Sc. Organic Chemistry entrance examination in Madras
University (A state wise entrance examination).
 Got 3rd
rank in B. Sc. Chemistry examination.
RESEARCH PUBLICATIONS
1. Indium(III) chloride catalyzed highly diastereoselective domino synthesis of
indenodithiepines and indenodithiocines, S. Muthusamy, M. Sivaguru, Chem.
Commu. 2015, 51, 707-710.
2. Atom-economical access to highly substituted indenes and Furan-2-ones via
tandem reaction of diazo compounds and propargyl alcohols, S. Muthusamy, M.
Sivaguru Organic Lett. 2014, 16, 4248-4251.
3. Synthesis of conformationally restricted symmetric macrodiolides via
carbonyl ylides, S. Muthusamy, M. Sivaguru, Synthesis, 2013, 45, 2034-2042.
4. Synthesis of conformationally restricted C2 symmetric macrodiolides via head
to tail dimerization of carbonyl ylides, S. Muthusamy, M. Sivaguru,
Tetrahedron Lett., 2013, 54, 6810-6813.
5. Synthesis of novel spiropyrrolidines through (3+2) cyclo addition reactions
with Baylis-Hillman adducts as dipolarophiles, J. Jayashankaran, R.S. Rathna
Durga. , M. Sivaguru, R. Ragunathan, Tetrahedron Lett., 2006, 47, 5535-5538.

3. 6. Synthesis of conformationally restricted macrocyclic bis-cyclopropanes in the
presence of copper catalyst, S. Muthusamy, M. Sivaguru (unpublished result)
7. Efficient approach to arylhydrazones, the precursor for 2,3-substituted indole
synthesis, via diazoamide, S. Muthusamy, M. Sivaguru (unpublished result).
CONFERENCE PAPERS/POSTERS
1. Poster presentation- Seminar on “Current Trends in Organic Synthesis” on June
19, 2013 held at Department of Chemistry, Madurai Kamaraj University,
Madurai, India.
2. Poster presentation- 12th
Chemical Research Society of India (CRSI) National
Symposium in Chemistry, February 4-7, 2010, Indian Institute of Chemical
Technology, Hyderabad, India-
3. Poster presentation- The mid-year meeting of the Chemical Research Society
of India, December 16-17 2011, Department of Chemistry, Pondicherry
University, Pondicherry, India.
4. RTOS-2011 volunteer- National conference on recent trends in organic
synthesis, February 24-26, 2011 held at Bharathidasan University,
Tiruchirappalli, Tamil Nadu, India.
5. National Symposium on “Recent Development in Chemistry” 29th
August, 2011,
School Of Chemistry, Bharathidasan University, Trichirappalli, Tamil Nadu,
India.
6. National Workshop on „Scholarly Information Access‟ on 23-24 October, 2009,
Bharathidasan University, Trichirappalli, Tamil Nadu, India.
TECHNICAL SKILLS
 Experience in handling Bruker 400 MHz NMR spectrometers and familiar with
two-dimensional NMR spectroscopy techniques.
 Experience with HPLC (Agilent)
 FT-IR (Bruker Alpha) and Digital Polarimeter (JASCO).
 Hands-on experience in handling of X-ray package Mercury.
 Expertise in the preparation and purification of organic molecules in mg to gram
scales.
TEACHING EXPERIENCE
Experience in conducting under-graduate level and graduate level laboratory work in
synthetic organic chemistry. Experience in guiding junior researchers, PhD students, M.
Phil. and project students.

4. API PROJECTS WORKED
Chemistry subject matter expert
I am working as a team leader for a group of 5 members and we are working for the
generation of chemistry research database. My job is to validate the data done by my
group members.
Tenofovir Alefanamide Hemi-Fumarate (anti-retroviral)
I have worked on the process development of tenofovir alefanamide hemi-fumarate. In
this process we have developed a catalyst/ligand free approach which will selectively
give 90 % pure diastereomeric isomer and <10 % of undesired isomer which further
removed during crystallization. In this project we faced problem in isolating hemi-
fumarate form still process are ongoing to get desired hemi-fumarate form.
Anacetrapib
Completed the process development of Anacetrapib (anti-cholesterol).
In this project we avoided the formation desmethyl API impurity by modified process
development to eliminate the impurity completely compared to innovator method. We
achieved 80% overall yield which is 10% more yield compared to other competitors.
Sunitinib & Valsartan
I worked on the process development of Sunitinib and Valsartan during my research
experience on Cadila pharmaceuticals. Our research group successfully carried out
technology transfer and process development on these molecules before the time line.
Donepezil Hydrochloride
In this project I carried out novel route for the formation of piperidone epoxide a key
intermediate for the formation of API which yielded one process patent in this molecule.
Similarly worked on the process development of Gemcitabine, Ezetimibe,
Temozolomide, Montelukest in Cipla pharmaceuticals.
EXPERIENCE IN REACTIONS
1. Synthesis of Boronic acids and Phosphate containing molecules
2. Ring opening of cyclopropane, epoxide.
3. Catalytic Hydrogenation
4. Lewis acid and organometallic reactions
5. Diazocarbonyl compounds and allene derivatives
6. Chiral reduction and Oxidation reactions
7. Bromination, Chlorination reactions
8. LDA, n-butyl Lithium, Grignard reactions, sodium metal, sodium amide,
sodium hydride etc.,

5. 9. Corrosive, lachrymatory and hygroscopic products
10. Having good experience on kilo lab batches
11. Liquid Nitrogen and Dry ice reaction (-76 C)
Personal Profile:
Father‟s Name : Late P. Manickasamy
Date of Birth : 10.09.1980
Nationality : Indian
Marital Status : Married
Languages Known : Tamil & English
Address for communication : 7/4A, Chandra Nivas
Amma Mandapam Road
Srirangam, Trichirappalli-620006.
Tamil Nadu, India.
REFERENCES
Dr. Venkataramana reddy Dr. J. Sony
Senior Research Scientist-1 Senior Research Scientist
Albany Molecular Research Center Ranbaxy Laboratories
Alexandria Knowledge Park, Genome Valley Guragon-122015
Turkapally, Hyderabad, India Haryana, India
venkataramanareddy.yemireddy@amriglobal.com josephsony@yahoo.com
+919610028340 +918285003062
prof. S. Muthusamy Dr. Vinod Acharya
School of Chemistry Group Leader-API R & D
Bharathidasan University Cipla Ltd.
Tiruchirapalli-620024 MIDC Patalganga Dist. Raigad
Tamil Nadu, India Maharashtra -410220
muthu@bdu.ac.in vinodacharya@rediffmail.com
+919442491933 +91880501494

6. DOCTORAL RESEARCH SUMMARY
In order to form C2 symmetric macrodiolide the required alkyne / alkene tethered diazocarbonyl
compounds 5 were assembled in a step-wise manner. Tandem reaction of -diazocarbonyl
compounds in the presence of rhodium(II) acetate catalyst was demonstrated to furnish
wide range of conformationally restricted C2 symmetric macrodiolides via head to tail
dimerization of carbonyl ylides.
O
O
R2
O
O
O
R1
Me
R2
O
OH
O
R1
Me
R2
O O
R1
Me
O
O
3
R1
, R2
= -(CH2)4-, -(CH2)3-
n = 1-3
toluene
reflux
OH
R2
O
R1
Me
O O O
( )n
( )n
MsN3,Et3N
DCM, rt
8% aqu
KOH
(i) [COCl]2
(ii) i-PrMgBr, THF
MeO2CCH2CO2H
DCM
R3
R3
R2
O
R1
Me
O O O
( )n
R3
N2
+
Rh2(OAc)4
O
O
Me
Me
Me
Me
Me
MeOO
OO
Me
Me
Me
O
O
O
Me
Me
Me
O
O
O
OO
O O
Rh2(OAc)4
R1
, R2
= CH3
n = 1-3
R1
, R2
= CH3
n = 1,3
R1
, R2
= CH3
n = Ar spacer
6 (3 examples)
6 (4 examples) 6 (2 examples)
n = 1-3
O
O
OO
OO
O O
Me
Me
( )n
( )n
( )n
( )n
O
O
Me
Me
Me
Me
Me
MeOO
OO
O
O
( )n
( )n
1 2
45
6
Tetrahedron letters, 2013, 54, 6810-6813
A series of bis-diazocarbonyl compounds 8 were assembled from transesterification reaction of
active methylene 3 with dihydroxy compounds in dry toluene followed by diazo transfer
reaction. Macrodiolides 11/12 incorporating oxa- and dioxa-fused units were synthesized from
bis-diazocarbonyl compounds 8 and bis-aldehyde / bis-olefin 9/10 as precursors to utilize the
bis-cycloaddition approach. Bis-olefin compounds 10 were obtained via Wittig reaction of the
corresponding bis-aldehydes 9. Initially, the reaction of bis-diazocarbonyl compounds 8 with
DMAD / NPM / aldehydes in the presence of rhodium(II) acetate dimer furnished bis-
cycloadduct 13-15.
O
O O O
( )n
toluene
reflux
Et3N, DCM
HO OH
( )n
O O
O O O O O O
( )n
O O
O O O O O O
N2 N2MsN3
O O
OO
Ph3PCH3Br
n-BuLi,THF
( )m
O O( )m
m = 3, 4, 6
n = 2-4, 8 83 7
9 10

7. Rh2(OAc)4
O
O O
OO
O
OO
O O
( )n
( )m
O
O
O O
OO
O
O
OO
O O
( )n
( )m
Rh2(OAc)4
(3 examples)
OO
OO ( )n
NN OOO
Ph Ph
(3 examples)
NPM
Rh2(OAc)4
O O
O OOO
OO ( )n
O O
O O
DMAD
Rh2(OAc)4
MeO2C CO2Me MeO2C CO2Me O
HH H H** * *
(7 examples)
O
O
O
O
OO
( )n
O O
O O
H H
R R
*
*
ArCHO;
Rh2(OAc)4
O O
O
OO
O
( )n
N2 N2
O
O
n = 2-4
m = 3, 4
n = 2, 3, 8
m = 3, 4, 6
n = 2-4 n = 2-4
n = 2-4
8
1112
13 14 15
Synthesis, 2013, 45, 2034-2042
The required bis-diazocarbonyl compounds 19/22 were also assembled via DCC coupling and
transesterification reaction. Bis-diazocarbonyl compound 24 was synthesized through N-
alkylation of diazoamides 23. After optimization, CuOTf was chosen for the bis-
cyclopropanation reaction between bis-diazocarbonyl compounds 19 and bis-olefin derivatives
11 to furnish conformationally restricted macrodiolide 25/26.
R
O
O
R
OH
O
+ HO OH DCC
O
R
O
( )n
MsN3
Et3N
DCM
O
O O
+
O
O O
O
toluene
( )n
R
O
O
O
R
O
( )n
N2 N2
HO OH
( )n
O O
( )n
MsN3
Et3N
DCM
O
O O
O
O O
( )n
N2 N2
reflux
DCM
19
22
N
N2
O
H
24
Br Br
N N
O O
N2N2
K2CO3/DMF
n = 2-4, 6
n = 3, 6
R = CO2Me, CO2Et, Ph
16 17 18
20 17 21
23
26 (9 examples)
O
O
O
O
O
O
( )m
( )n
O O
19/22
CuOTf
Toluene
R R
( )m
NN
O O
OO
25 (2 examples)
24
CuOTf
Toluene
m =3-6, 8 n =2-4, 6
R = CO2Me, CO2Et, COMe,Ph
( )m
+ +
11
Unpublished results

8. Reaction of diazoamide 27 was treated with 1 equiv of Grignard reagents to give hydrazone
incorporating oxindole 28 in excellent yield. Similar reaction was performed with diazoester 33
and cyclohexanone diazo compounds 31 to furnish 34/32. Thus, the diazoamide 27 was treated
with 2.5 equiv. Grignard reagents to furnish 2-phenyl-3-azoindole derivative 29 in excellent
yield. Reduction of azo compounds 29 carried out using SnCl2 in AcOH to their respective
amino compounds 30.
N
O
HN
R'
N2
O
rtOMe
OMe
+ R'MgX THF
N
N
O
HN
R'
R
N
N2
O
R
excess R'MgX
THF, 30 °C
1.2 eqiv. R'MgX
THF, 30 °C
N
N
R'
N
R'
R
29 (9 examples)
N
NH2
Me
AcOH
SnCl2
30 (2 examples)
(8 examples)
O
N
N
H
rt
+ R'MgX
THF
O
N2
27 R = H, Allyl,
Me, Et, Bn
28 R' = Ph, i-pr, Cyclohexyl
31 32
33 34
Unpublished results
An atom-economical facile synthesis of highly substituted as well as conjugated indene
36 /furanone 37 systems via BF3.OEt2 catalyzed tandem reaction of -diazo-esters 33 /-
amides 27 and propargyl alcohols 35 has been demonstrated under mild conditions. This
methodology offers a great potential for the synthesis of biologically active indene 36
and furanone 37 derivatives and their related polycyclic compounds.
CO2R4
N2CO2R4
R1
O
R1
NH
R6 O
N
N2
O
R6
R3
R2
R1
OH
R2
R3R3
R2
R5
BF3.OEt2
DCM, 0 °C
BF3.OEt2
DCM, 0 °C
R5
36 (16 examples) 37 (10 examples)
C
CO2Me
OH
Rh2(OAC)4
33
33R1
= Ph, tolyl, cyclopropyl,
n-butyl, n-heptyl
R2
= H, F, Cl, Me, OMe
R3
= H, F, Cl, Me
R4
= Me,Et, Bu, allyl
propargyl
R1
= Ph, tolyl, cyclopropyl,
n-butyl, n-heptyl
R2
= H, F, Cl, Me, OMe
R3
= H, F, Cl, Me
R5
= Me,Et, Bn, allyl
R1
= Ph
R2
, R3
, R5
, = H
R4
= Me
27
35
38
Organic Letters 2014, 16, 4248-4251

9. An diastereoselective synthesis of indenodithiepines 40 and indenodithiocines has been
developed via tandem reaction of propargylic alcohols 35 and dithioacetals 39 in the
presence of InCl3 as a catalyst. A range of functionalized dithiepines and dithiocines,
fused to indene ring, were obtained in good to excellent yields under mild conditions.
Further indenodithiepine was smoothly oxidized to the corresponding sulfone by
refluxing with H2O2/AcOH
OH
S
S
InCl3
DCE, 80 °C
R1
R1
R1 ( )n+
SS
( )n
R1
H2O2/AcOH
reflux, 30 min
S
S
CF3
O
O
O O
40 (18 examples)35 R1
= H, F, Cl, Me
39 R2
= H, Cl, Br, Me, OMe,
CN, Br, Cl, F, NO2, napthyl
R2
n = 0,1
41
R2
Chemical Communication 2015, 51, 707-710