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Total Synthesis of Everninomicin 13,384‐1—Part 1: Synthesis of the A 1 B(A)C Fragment
Author(s) -
Nicolaou K. C.,
Mitchell Helen J.,
Suzuki Hideo,
Rodríguez Rosa Maria,
Baudoin Olivier,
Fylaktakidou Konstantina C.
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(19991115)38:22<3334::aid-anie3334>3.0.co;2-h
Subject(s) - fragment (logic) , chemistry , total synthesis , stereochemistry , computer science , algorithm
The powerful antibiotic everninomicin 13,384‐1 ( 1 , Ziracin) has been prepared for the first time through a total synthesis. The 1→1′‐disaccharide and the two orthoesters of this target molecule were introduced by new methodologies using a tin acetal and 1,2‐phenylseleno migrations. The reaction sequence also relies on stereoselective glycosidations and subtle manipulations of protecting groups. In addition to the introduction of new synthetic methodologies, this total synthesis should allow the preparation of combinatorial libraries of semisynthetic analogues of this highly promising antibiotic for biological screening purposes.