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A Total Synthesis of Aphidicolin: Stereospecific Synthesis of (±)-3α, 18-Dihydoxy-17-Noraphidicolan-16-one

✍ Scribed by Rinaldo Marini Bettolo; Pietro Tagliatesta; Alessandro Lupi; Doriano Bravetti

Publisher
John Wiley and Sons
Year
1983
Tongue
German
Weight
423 KB
Volume
66
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

A simple, efficient, and stereospecific total synthesis of (±)‐3α, 18‐dihydroxy‐17‐noraphidicolan‐16‐one (2), by solvolytic rearrangement of the endo‐bicyclo‐[2.2.2]oct‐5‐en‐2‐yl methanesulfonate 16, is described. Since aphidicolin (1) has already been obtained from 2, the preparation of the latter formally constitutes a new total synthesis of 1.

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