Steyn, P.S.Botha, Jeanne H.Breytenbach, JacoFernandes, M.A.Wessels, P.L.2010-05-212010-05-212008Steyn, P.S. et al. 2008. Synthesis, complete 1H and 13C NMR assignment and crystal structure of novel epoxide derivatives of cytochalasin B. Magnetic resonance in chemistry, 46(7):650-659. [https://doi.org/10.1002/mrc.2227]http://hdl.handle.net/10394/3062https://onlinelibrary.wiley.com/doi/abs/10.1002/mrc.2227https://doi.org/10.1002/mrc.2227Five 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.enArticle