Issue 3, 2011

Benzoylureas as removable cisamide inducers: synthesis of cyclic amidesviaring closing metathesis (RCM)

Abstract

Rapid and high yielding synthesis of medium ring lactams was made possible through the use of a benzoylurea auxiliary that serves to stabilize a cisoidamide conformation, facilitating cyclization. The auxiliary is released after activation under the mild conditions required to deprotect a primary amine, such as acidolysis of a Boc group in the examples given here. This methodology is a promising tool for the synthesis of medium ring lactams, macrocyclic natural products and peptides.

Graphical abstract: Benzoylureas as removable cis amide inducers: synthesis of cyclic amidesvia ring closing metathesis (RCM)

Supplementary files

Article information

Article type
Communication
Submitted
15 Sep 2010
Accepted
25 Oct 2010
First published
18 Nov 2010

Org. Biomol. Chem., 2011,9, 656-658

Benzoylureas as removable cis amide inducers: synthesis of cyclic amidesvia ring closing metathesis (RCM)

R. M. Brady, Y. Khakham, G. Lessene and J. B. Baell, Org. Biomol. Chem., 2011, 9, 656 DOI: 10.1039/C0OB00723D

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