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Synthesis of the Southern FGHI Ring System of Azaspiracid‐1 and Investigation into the Controlling Elements of C28‐ and C36‐Ketalization
Author(s) -
Zhou XiaoTi,
Lu Liang,
Furkert Daniel P.,
Wells Charles E.,
Carter Rich G.
Publication year - 2006
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.200603353
Subject(s) - stereocenter , chemistry , trimethylsilyl , ring (chemistry) , stereochemistry , combinatorial chemistry , organic chemistry , enantioselective synthesis , catalysis
Heading south : An efficient approach to the FGHI southern ring system of azaspiracid‐1 is disclosed. Each of the eight stereogenic centers is generated with excellent diastereoselectivity. In addition, the stereochemical outcome of the ketalization steps could be controlled by careful selection of the conditions. Teoc=2‐(trimethylsilyl)ethoxycarbonyl; TMS=trimethylsilyl; TIPS=triisopropylsilyl; Bn=benzyl.