MODEL STUDIES TOWARDS THE TOTAL SYNTHESIS OF THE STEMONA ALKALOID 1-HYDROXYPROTOSTEMONINE: SYNTHESIS OF ENT-1-HYDROXYSTEMOAMIDE

摘要

As part of a model study towards the total synthesis of Stemona alkaloid 1-hydroxyprotostemonine 1, we have achieved the synthesis an A-B-C ring precursor, ent-1-hydroxystemoamide. Key steps involve an ene-yne RCM reaction and a diastereoselective dihydroxylation-lactonization reaction. This paper is dedicated to Prof. Al Padwa on the occasion of his 75th birthday in recognition of his many valuable contributions to heterocyclic chemistry.