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Synthesis, complete 1 H and 13 C NMR assignment and crystal structure of novel epoxide derivatives of cytochalasin B
Author(s) -
Steyn Pieter S.,
Breytenbach Jaco C.,
Botha Jeanne H.,
Fernandes Manuel A.,
Wessels Philippus L.
Publication year - 2008
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/mrc.2227
Subject(s) - chemistry , epoxide , double bond , stereochemistry , absolute configuration , cytochalasin d , single crystal , organic chemistry , crystallography , catalysis , biochemistry , cytoskeleton , cell
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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