Synthesis, complete 1H and 13C NMR assignment and crystal structure of novel epoxide derivatives of cytochalasin B
Date
2008Author
Steyn, P.S.
Botha, Jeanne H.
Breytenbach, Jaco
Fernandes, M.A.
Wessels, P.L.
Metadata
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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.
URI
http://hdl.handle.net/10394/3062https://onlinelibrary.wiley.com/doi/abs/10.1002/mrc.2227
https://doi.org/10.1002/mrc.2227
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