The Compounds Limits of Detection, Molecules of Only One Chirality Synthesis of (+)-Monomorine Using a 5-Endo-Trig Cyclization Strategy

Rajvinder Kaur

The Compounds Limits of Detection, Molecules of Only One Chirality Synthesis of (+)-Monomorine Using a 5-Endo-Trig Cyclization Strategy

A Strategy for the Synthesis of (+)-Monomorine Using 5-Endo-Trig Cyclization

by Rajvinder Kaur*,

- Published in Journal of Advances in Science and Technology, E-ISSN: 2230-9659

Volume 1, Issue No. 1, Feb 2011, Pages 0 - 0 (0)

Published by: Ignited Minds Journals

ABSTRACT

We have developed a general strategy for thesynthesis of 2,5-syn disubstituted pyrrolidines that is based on themulti-faceted reactivity of the sulfone moiety and a 5-endo-trig cyclisation.This methodology was applied to the synthesis of indolizidine alkaloidmonomorine I. Two factors were key to the success of this endeavour; the firstwas the choice of nitrogen protecting group whilst the second was theconditions for the final stereoselective amination step. Employing acombination of different protecting groups and an intramolecular reductiveamination reaction we were able to prepare (+)-monomorine I in just 11 stepsfrom commercially available D-norleucine in a completely stereoselectivemanner.

KEYWORD

limits of detection, molecules of only one chirality, synthesis, 5-endo-trig cyclization strategy, 2,5-syn disubstituted pyrrolidines, sulfone moiety, indolizidine alkaloid monomorine I, nitrogen protecting group, stereoselective, amination reaction