title: Synthesis, complete 1H and 13C NMR assignment and crystal structure of novel epoxide derivatives of cytochalasin B.
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.
authors.affiliation: Director: Research (Science), University of Stellenbosch, Private Bag X1, Matieland, 7602, South Africa.
authors.forename: Pieter S
authors.initials: PS
authors.lastname: Steyn
authors.forename: Jaco C
authors.initials: JC
authors.lastname: Breytenbach
authors.forename: Jeanne H
authors.initials: JH
authors.lastname: Botha
authors.forename: Manuel A
authors.initials: MA
authors.lastname: Fernandes
authors.forename: Philippus L
authors.initials: PL
authors.lastname: Wessels
mesh_terms: D002247:Carbon Isotopes; D018360:Crystallography, X-Ray; D003571:Cytochalasin B / Q000737:chemistry*; D004852:Epoxy Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D015394:Molecular Structure; D011522:Protons
chemical_list: D002247:Carbon Isotopes; D004852:Epoxy Compounds; D011522:Protons; D003571:Cytochalasin B