Stereoselective Preparation of Cyclobutanes with Four Different Substituents: Total Synthesis and Structural Revision of Pipercyclobutanamide A and Piperchabamide G | Zendy

Liu Renhe | Zendy; Zhang Min | Zendy; Wyche Thomas P. | Zendy; WinstonMcPherson Gabrielle N. | Zendy; Bugni Tim S. | Zendy; Tang Weiping | Zendy

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Stereoselective Preparation of Cyclobutanes with Four Different Substituents: Total Synthesis and Structural Revision of Pipercyclobutanamide A and Piperchabamide G

Author(s) -

Liu Renhe,

Zhang Min,

Wyche Thomas P.,

WinstonMcPherson Gabrielle N.,

Bugni Tim S.,

Tang Weiping

Publication year - 2012

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.201203379

Subject(s) - cyclobutanes , cyclopropanation , enantioselective synthesis , regioselectivity , stereospecificity , chemistry , stereoselectivity , stereochemistry , ring (chemistry) , total synthesis , catalysis , combinatorial chemistry , organic chemistry , cycloaddition

Squared away : A general strategy was developed for the diastereo‐ and enantioselective synthesis of cyclobutanes having four different substituents (see scheme). The strategy involves a Rh II ‐catalyzed cyclopropanation, a Ag I ‐catalyzed regioselective and stereospecific ring expansion, and a Rh I ‐catalyzed addition reaction. The structures of pipercyclobutanamide A and piperchabamide G were synthesized and revised.

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