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