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Concise Enantioselective Synthesis of (+)‐FR66979 and (+)‐FR900482: Dimethyldioxirane‐Mediated Construction of the Hydroxylamine Hemiketal
Author(s) -
Judd Ted C.,
Williams Robert M.
Publication year - 2002
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200290015
Subject(s) - dimethyldioxirane , enantioselective synthesis , hydroxylamine , chemistry , ring (chemistry) , stereochemistry , epoxide , propiophenone , ketone , organic chemistry , catalysis
The remarkable one‐step deprotection/oxidative cyclization of an eight‐membered‐ring aminoketone 1 in the presence of dimethyldioxirane gives rise to the unique hydroxylamine hemiketal ring system of FR66979 ( 2 ) and FR900482 ( 3 ), clinically important antitumor antibiotics. The concise 33‐step enantioselective synthesis of 3 is the shortest route reported to date.