Longifolene is common naturally occurring, oily liquid hydrocarbon found in the high boiling fraction of certain pine resins. Juvabione is a terpene- derived-keto-ester that has been isolated from plant sources. Morphine is a major component of opium,it is isolated from poppy straw of the opium poppy.

1. Disconnection Approach
Towards Longifolene, Juvabione
and Morphine
Presented By
Beena
Rollno.
180000701011
M. Sc. Chemistry (F)
Under supervision
Dr. Maynak Kinger
Associate Professor
Department Of Chemistry
CBLU,Bhiwani

2. Contents
1. Introduction
2. Longifolene
3. Disconnection approach towards Longifole
4. Synthesis of Longifolene
5. Merits of longifolene
6. Juvabione
7. Disconnection approach towards Juvabione
8. Synthesis of Juvabione
9. Merits of Juvabione
10. Morphine
11. Structure of Morphine
12. Disconnection approach towards Morphine
13. Synthesis of morphine
14. Merits of Morphine
15. Demerits of Morphine
16. References

3. 1. Introduction
Disconnection approach or Retrosynthesis:
A logical approach for designing organic synthesis
which involves breaking down of the target molecule
in to available starting material by imaginary breaking
of bonds or by FGI .
For example

4. 2. Longifolene
Longifolene is common naturally
occurring,oily liquid hydrocarbon found in the
high – boiling fraction of certain pine resins.
Chemically Longifolene is a tricyclic
sesquitrephene.

5. 3. Disconnection approach towards
Longifolene
 Retrosynthetic Analysis :-

6. Continue
 For this disconnection to correspond to a
reasonable synthetic step ,the functionality on C-7
and C-10 in the intermediate must be suitable for
cyclisation.
Diketone (2) achieved because an enolate generated
by deprotection at C-10 can undergo intramolecular
Michael addition to C-7.
Retrosynthetic step (2) (3) is attractive.The
transformation of hydroxyl to carbonyl group with
migration corresponds to the pinacol- pinacolone
rearrangement.

7. 4. Synthesis of Longifolene
Forward synthesis :- first successful synthesis
described in detail by E.J.Corey and co-workers.

8. 5. Merits of Longifolene
The borane derivative dilongifolylborane
is used in organic synthesis as a chiral
hydroborating agent.

9. 6. Juvabione
 Juvabione is a terpene – derived keto –ester
that has been isolated from
plant sources. There are two stereisomer,both
of which occur
naturally with R Configuration.

10. 7. Disconnection approach toward Juvabione
 Retrosynthetic analysis:- The C-4 and C-7 carbons are chiral .The
C(4) – C(7) bond also connect the side chain to the cyclohexene
ring.because a cyclohexene derivative would make a logical
candidate for one key intermediate,the C(4)-C(7) bond is a
potential disconnection.The disconnection is that of ester
functionality.

11. Continue
Disconnection 2 identifies the C(9)-C(10) bond as that can be
readily formed by addition of some nucleophilic group
corresponding to C(10)-C(13) to the carbonyl centre at C-9
Third retrosynthetic transform recognises that cyclohexane ring
might be obtained by Birch reduction of substituted aromatic
ether.
The final disconnection Identifies a simple starting material, 4-
methoxyacetophenone.

12.  K.Mori and M. Matsui synthesis : -
8. Synthesis of Juvabione

13. Continue
The C(4)-C(7) bond is formed by a Refornatsky reaction,and
this is followed by benzylic hydrogenolysis. Steps B and C
introduce the C10 – C13 isobutyl group. The C(9)-C(10)
bond connection is done in step C by a grignard addition
reaction. In this synthesis,the relative configuration at C-4
and C-7 is established by the hydrogenation in step E.
This reaction could be diasteroselective if the adjacent
stereo centre at C-7 strongly influenced the direction of
addition of hydrogen.

14. 9. Merits of Juvabione
 Sesquitrephenes of juvabione family are known as
insect juvenile hormone analogues because of their
ability to mimic juvenile activity in order to stifle
insect reproduction and growth.
These compound play important
roles in coniters as the second line of
defense against insect induced trauma and
fungal pathogens.

15. 10. Morphine
 Morphine is the major component of opium
,representing 10 – 15% of its dry weight . The primary
Source of morphine is isolation from poppy straw of
the opium poppy.
The crystalline morphine was first
Isolated by Friedrich Sertumer in
1804, and was first commercially
Produced by Merck in 1827.

16. 11. Structure
 Morphine have complicated pentacycllic Skelton
including five steteogenic centre ,an ether bridge and
a piperidine ring. Morphine have two enantiomers

17. 12. Disconnection approach to
Morphine
Retrosynthetic analysis :-

18. 13. Synthesis of Morphine
 Gates’ total synthesis of morphine proposed by
Robison in 1925.

19. 14. Merits of Morphine
 Morphine most widely used as a drug in
medical prupuse.It have many advantages over
other drugs:-
1. It can taken for both acute pain and
chronic pain.
2. It act directly on the central nervous
system.
3. Used as a slow release formulation for
opiate substitution therapy.

20. 15. Demerits/side effects of
Morphine
 Morphine have some following side effect
1. Morphine is addictive and prone
to abuse.
2. Morphine cause hormone
imbalance.
3. It cause potentially serious side effect
include decreased respiratory effort and low blood
pressure.

21. 16. References
1. Kathlyn A. Parker and Demosthenes
Fokas; Enantioselective synthesis of.
(-)- Dihydrocodeinone: A shor
formal synthesis of (-)- Morphine; June
24,2005.
2. https: //en.m.wikipedia.org
3. Jagdamba Singh and L.D.S. Yadav ; Organic
synthesis ; vol.11;2015