Open AccessEnantioselective Synthesis of (+)-Cephalostatin 1
Author(s) -
Kevin C. Fortner,
Darryl Kato,
Yoshiki Tanaka,
Matthew D. Shair
Publication year - 2009
Publication title -
journal of the american chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 7.115
H-Index - 612
eISSN - 1520-5126
pISSN - 0002-7863
DOI - 10.1021/ja906996c
Subject(s) - chemistry , enantioselective synthesis , hydroxylation , allylic rearrangement , stereochemistry , sterol , catalysis , organic chemistry , enzyme , biochemistry , cholesterol
This Article describes an enantioselective synthesis of cephalostatin 1. Key steps of this synthesis are a unique methyl group selective allylic oxidation, directed C-H hydroxylation of a sterol at C12, Au(I)-catalyzed 5-endo-dig cyclization, and a kinetic spiroketalization.
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