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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

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posted on 2006-01-19, 00:00 authored by Madhumita 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.

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