Issue 4, 2013

A photoisomerization-coupled asymmetric Stetter reaction: application to the total synthesis of three diastereomers of (−)-cephalimysin A

Abstract

The total synthesis of 8-epi, 8,9-epi, and 9-epi-(−)-cephalimysin A is described. Our catalytic enantioselective synthesis takes advantage of a novel tandem photoisomerization/Stetter reaction. The approach provides rapid access to the desired spirofuranone lactam core in good yield and excellent enantioselectivity. A late stage oxidation strategy allows for flexible access to three of the four diastereomers of cephalimysin A. Access to the epimers provides further support for the correction of the initially proposed relative stereochemistry of cephalimysin A.

Graphical abstract: A photoisomerization-coupled asymmetric Stetter reaction: application to the total synthesis of three diastereomers of (−)-cephalimysin A

Supplementary files

Article information

Article type
Edge Article
Submitted
20 Dec 2012
Accepted
13 Feb 2013
First published
22 Feb 2013

Chem. Sci., 2013,4, 1668-1673

A photoisomerization-coupled asymmetric Stetter reaction: application to the total synthesis of three diastereomers of (−)-cephalimysin A

S. P. Lathrop and T. Rovis, Chem. Sci., 2013, 4, 1668 DOI: 10.1039/C3SC22292F

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