INTRODUCTION

LITERATURE REVIEW
OBJECTIVE OF THE WORK SYNTHETC ROUTE PLAN WORK DONE CHARACTERISATION DATA

FUTURE WORK
REFERENCES

Functionalised pipyridines are found to exhibit good biological activity of medicinal interest.

A large no. of synthetic designs for this ring system has been developed day to day.
Among These various naturally occuring compounds are (+)- Prosopinine, (-)-Prosophyline , which are isolated from leaves of prosopis africana taub, possess antibiotic and aneasthetic property and (-)-Sedacryptine, (+)-Isofebrifugine.alkaloids shows anti malarial activity against plasmodium falciparam.As a result these natural products becomes interested as synthetic targets.

The following natural products have been synthesised using cyclohydro carbonylation protocol to achieve enantio pure pipyridine intermediate and there by they introduced long alkyl chain at C-6 position in previous report.

J.Org.Chem.1998,63,7999-8003

In Previous report The synthesis of (+)-Isofebrifugine, and (-) Sedacryptine starting from (3). And the utility of (3) for the synthesis of these natural products demonstrate the flexybility of the approach which provides ready access to both 2substituted and 2,6-di substituted 3- hydroxy pipyridine alkaloids.

Using bridged oxozolidine of pipyridine derivative as an intermediate proposed a synthetic route to various natural products.

And the intermediate proposed have been synthesised starting from garners aldehyde.

Garners aldehyde has been synthesised from L-Serine

Starting from garners aldehyde two steps have completed and the next step is in under optimisation.

I am facing problems in achieving bridged oxozolidine of pipyridine derivative . During the synthesis of (3), imine(2) is an intermediate.The isolation of this intermediate is very difficult task.I performed the deprotection of (1) in following conditions

S.N0

REACTION CONDITION

1 2

10% HCl 6NHCl

PROGRESS ON TLC IN 40% EtOAC PROGRESSED WITH ZERO Rf PROGRESSED

MASS -

1HNMR

NOT CLEAR SHOWS M+1 PEAK SHOWS M+1 PEAK SHOWS M+1 PEAK NOT CLEAR

12N HCl

PROGRESSED

NOT UNDERSTOOD NOT CLEAR

TFA

PROGRESSED

With strong acid, deprotection step of(1) not achieved effectively.So we planned step wise deprotection.And the proposed synthetic route is shown below.

With 80%AcOH We achieved (4) and is confirmed by 1HNMR ,13C NMR, And by mass(m+23) But catalytic amt of PTSA in acetone with (4) as starting material results fully deprotected compound(6). And that is confirmed by mass (M+1).

So with Fmocl we planned for protection of (6). On TLC it shows progress .A Pink spot has been observed with 0.4 rf in 30%EtOAC. Mass shows(M+1) Peak.