Asymmetric Synthesis of N,O-Heterobicyclic Octanes and (−)-Geissman–Waiss Lactone

ACS Omega
2021.0

Abstract

A short, asymmetric synthesis of tetrahydro-2H-furo[3,2-b]pyrrole derivatives and (-)-Geissman-Waiss lactone starting from meso-cyclohexadiene epoxide is described. Pivotal transformations in the developed synthetic procedure include asymmetric epoxide ring opening to install the requisite 1S,5S stereocenters and oxidative lactonization/lactamization sequences. This route provides a streamlined synthetic pathway toward necine alkaloids. CI - (c) 2021 The Authors. Published by American Chemical Society.

DOI： 10.1021/acsomega.1c03251

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