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Total Synthesis of Neooxazolomycin
Author(s) -
Onyango Evans Otieno,
Tsurumoto Joji,
Imai Naoko,
Takahashi Keisuke,
Ishihara Jun,
Hatakeyama Susumi
Publication year - 2007
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.200702229
Subject(s) - dihydroxylation , hydrosilylation , stereoselectivity , stereochemistry , palladium , chemistry , combinatorial chemistry , enantioselective synthesis , catalysis , organic chemistry
Two sides to the story : Neooxazolomycin, a member of the oxazolomycin family of antibiotics, was synthesized in naturally occurring form by a convergent approach. This highly stereoselective strategy consists of a Tamao hydrosilylation, palladium‐catalyzed enolate alkenylation, dihydroxylation accompanied by lactonization, and a Nozaki–Hiyama–Kishi reaction to construct the right‐hand segment as well as an improved route to the left‐hand segment.