Journal article

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

Ryan M Brady, Yelena Khakham, Guillaume Lessene, Jonathan B Baell

Organic & Biomolecular Chemistry | ROYAL SOC CHEMISTRY | Published : 2011

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 cisoid amide 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.

Grants

Awarded by NHMRC IRISS


Funding Acknowledgements

This work was supported by the NHMRC IRISS Grant 361646 and a Victorian State Government OIS grant