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Interplay of Cascade Oxidative Cyclization and Hydride Shifts in the Synthesis of the ABC Spiroketal Ring System of Pectenotoxin‐4
Author(s) -
Donohoe Timothy J.,
Lipiński Radosław M.
Publication year - 2013
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.201208919
Subject(s) - hydride , sequence (biology) , stereochemistry , cascade , chemistry , scheme (mathematics) , combinatorial chemistry , fragment (logic) , computer science , programming language , mathematics , organic chemistry , biochemistry , hydrogen , chromatography , mathematical analysis
Concepts : The formation of stereochemically defined bis‐THF units through a double cyclization and a hydride‐shift‐initiated route to spiroketals is described (see scheme; Xc=chiral auxiliary). The resulting sequence has been used in a synthesis of the C1–16 fragment of the naturally occurring antitumor agent pectenotoxin‐4.