Divergent Cycloaddition and
Ring-Closing Metathesis Approaches to
Indolizidine and Pyrrolo[1,2-a]azepine
Skeletons from a Chiral Precursor:
An Expeditious Route to
(−)-8-epi-Swainsonine Triacetate
posted on 2006-01-19, 00:00authored byMadhumita Nath, Ranjan Mukhopadhyay, Anup Bhattacharjya
A divergent strategy for the synthesis of diverse azabicyclic ring systems has been developed in which a chiral N-allylpyrrolidine derivative,
obtained from a carbohydrate precursor was converted to (−)-8-epi-swainsonine triacetate by RCM and to a pyrrolo[1,2-a]azepine derivative
and a 3-hydroxymethyl-substituted indolizidine by N-allylcarbohydrate nitrone and nitrile oxide cycloadditions.