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Total Synthesis of Antascomicin B
Author(s) -
Brittain Dominic E. A.,
GriffithsJones Charlotte M.,
Linder Michael R.,
Smith Martin D.,
McCusker Catherine,
Barlow Jaqueline S.,
Akiyama Ryo,
Yasuda Kosuke,
Ley Steven V.
Publication year - 2005
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.200500174
Subject(s) - enantioselective synthesis , polyketide , total synthesis , catechol , stereochemistry , chemistry , key (lock) , combinatorial chemistry , biology , organic chemistry , catalysis , ecology , enzyme , biosynthesis
The structurally enticing antascomicin B ( 1 ), which exhibits potent immunosuppressant‐antagonizing properties, has a complex polyketide structure. Key steps in its enantioselective total synthesis include a transannular catechol‐templated Dieckmann reaction to assemble the challenging tricarbonyl functionality and a butanediacetal‐directed allylation.