A concise synthesis of (±) and a total synthesis of (+)-epiquinamide

STA Tong, D Barker

Index: Tong, Sok Teng (Amy); Barker, David Tetrahedron Letters, 2006 , vol. 47, # 29 p. 5017 - 5020

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Citation Number: 33

Abstract

A total synthesis of the quinolizidine alkaloid (+)-epiquinamide 1 has been achieved starting from (−)-pipecolinic acid 3. The key step is the highly diastereoselective addition of a TBDMS-protected propargyl alcohol to a chiral aldehyde derived from 3 to give erythro alkynol 19, which is then easily transformed into the desired bicyclic skeleton.