Concise Enantioselective Synthesis of (+)‐FR66979 and (+)‐FR900482: Dimethyldioxirane‐Mediated Construction of the Hydroxylamine Hemiketal | Zendy

Judd Ted C. | Zendy; Williams Robert M. | Zendy

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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.

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