Affiliation:
1. Department of Chemistry, Tokyo Institute of Technology
Abstract
A general synthetic approach to rotenoids is described, featuring 1) stereospecific, group-selective 1,2-rearrangements of epoxy alcohols, and 2) SNAr oxy-cyclizations of aryl fluorides. The common intermediate epoxyketone, en route to (–)-rotenone and (–)-deguelin, was prepared from d-araboascorbic acid in five steps. Also described is the conversion of (–)-deguelin into oxidized congeners, (–)-tephrosin and (+)-12a-epi-tephrosin.
Funder
Japan Society for the Promotion of Science
Subject
Organic Chemistry,Catalysis
Cited by
5 articles.
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