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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.