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Synthesis, complete 1H and 13C NMR assignment and crystal structure of novel epoxide derivatives of cytochalasin B

✍ Scribed by Pieter S. Steyn; Jaco C. Breytenbach; Jeanne H. Botha; Manuel A. Fernandes; Philippus L. Wessels

Publisher
John Wiley and Sons
Year
2008
Tongue
English
Weight
194 KB
Volume
46
Category
Article
ISSN
0749-1581

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✦ Synopsis

Abstract

Five novel epoxide derivatives of cytochalasin B were synthesized. Reaction of cytochalasin B with t‐BHP and BuLi led to selective epoxidation of the C‐21/22 double bond to give a single monoepoxide, while reaction with m‐CPBA yielded two diepoxides. Reaction of the monoepoxide with m‐CPBA yielded two triepoxides. The relative configurations of the epoxides were elucidated by analogy with the natural product by means of spectroscopic methods; full assignment of NMR signals was achieved, and the absolute configuration was confirmed by X‐ray crystallography. Copyright © 2008 John Wiley & Sons, Ltd.

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