Total Synthesis of (±)-Quebrachamine via [3+2] Cycloaddition and Efficient Chloroacetamide Photocyclization

Authors

Brian Pagenkopf, University of Western OntarioFollow
Barbora Bajtos

Document Type

Article

Publication Date

1-14-2009

Journal

European Journal of Organic Chemistry

Volume

2009

Issue

7

First Page

1072

Last Page

1077

URL with Digital Object Identifier

10.1002/ejoc.200801154

Abstract

The total synthesis of (±)-quebrachamine has been completed in 13 linear steps and 17.8 % overall yield. The indole core was constructed via a formal [3+2] dipolar cycloaddition between a functionalized nitrile and donor-acceptor cyclopropane, and the synthetically challenging nine-membered ring was secured by an efficient chloroacetamide photocyclization.