Total Synthesis of Antascomicin B | Zendy

Brittain Dominic E. A. | Zendy; GriffithsJones Charlotte M. | Zendy; Linder Michael R. | Zendy; Smith Martin D. | Zendy; McCusker Catherine | Zendy; Barlow Jaqueline S. | Zendy; Akiyama Ryo | Zendy; Yasuda Kosuke | Zendy; Ley Steven V. | Zendy

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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.

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