Work

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

Year: 2012

Type: article

Abstract: 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 RhII-catalyzed cyclopropanation, a AgI-catalyzed regioselective and stereospecific ring expansion, and a RhI-catalyzed addition reaction. The structures of pipercyclobutanamide A and piperchabamide G were synthesized and revised.

Source: Angewandte Chemie International Edition

DOI: 10.1002/anie.201203379

Authors: Renhe Liu, Min Zhang, Thomas P. Wyche, Gabrielle N. Winston‐McPherson, Tim S. Bugni, Weiping Tang

Institution: University of Wisconsin–Madison

Language: English

Topic: Cyclopropane Reaction Mechanisms

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: National Institute of General Medical Sciences, National Center for Research Resources