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Total Synthesis of Sanglifehrin A
Author(s) -
Nicolaou K. C.,
Xu Jinyou,
Murphy Fiona,
Barluenga Sofia,
Baudoin Olivier,
Wei Hengxu,
Gray David L. F.,
Ohshima Takashi
Publication year - 1999
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/(sici)1521-3773(19990816)38:16<2447::aid-anie2447>3.0.co;2-o
Subject(s) - stille reaction , intramolecular force , total synthesis , aldol reaction , intermolecular force , acetal , stereochemistry , chemistry , unit (ring theory) , combinatorial chemistry , molecule , organic chemistry , mathematics , catalysis , mathematics education
The immunosuppressive agent sanglifehrin A has been prepared for the first time by total synthesis. The construction of the macrocyclic unit of the target molecule was achieved through a selective intramolecular Stille coupling, and the spirolactam unit by Paterson–aldol reactions. The final steps involve an intermolecular Stille coupling and the opening of the internal acetal unit. This convergent synthesis opens the way for the synthesis of libraries of novel sanglifehrin analogues for biological screening.