Tetrahedron

The synthesis of ascididemin

CJ Moody, CW Rees, R Thomas

Index: Moody, Christopher J.; Rees, Charles W.; Thomas, Robert Tetrahedron, 1992 , vol. 48, # 17 p. 3589 - 3602

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Citation Number: 42

Abstract

A short synthsis of the pentacyclic marine alkaloid ascididemin 1 (four steps, 21% yield) from 1, 10-phenanthroline 16 is described. The key step, photocyclisation of the quinoneimine 14 in sulphuric acid, is the first such aza stilbene photocyclisation of a quinoneimine. Intermediate 14 is prepared in a single, but low yielding, step from the quinone 4 in an aza Wadsworth-Emmons reaction, or in much better yield from the epoxide 17 by treatment ...

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