Synthesis, complete 1H and 13C NMR assignment and crystal structure of novel epoxide derivatives of cytochalasin B.
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.
Steyn
Pieter S
PS
Director: Research (Science), University of Stellenbosch, Private Bag X1, Matieland, 7602, South Africa.
Breytenbach
Jaco C
JC
Botha
Jeanne H
JH
Fernandes
Manuel A
MA
Wessels
Philippus L
PL
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
D002247:Carbon Isotopes; D004852:Epoxy Compounds; D011522:Protons; D003571:Cytochalasin B