Interplay of Cascade Oxidative Cyclization and Hydride Shifts in the Synthesis of the ABC Spiroketal Ring System of Pectenotoxin‐4 | Zendy

Donohoe Timothy J. | Zendy; Lipiński Radosław M. | Zendy

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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.

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