Benzoylureas as removable cis amide inducers: synthesis of cyclic amides via ring closing metathesis (RCM)
- Author(s)
- Brady, RM; Khakham, Y; Lessene, G; Baell, JB;
- Details
- Publication Year 2011,Volume 9,Issue #3,Page 656-658
- Journal Title
- ORGANIC & BIOMOLECULAR CHEMISTRY
- Publication Type
- Journal Article
- 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.
- Publisher
- ROYAL SOC CHEMISTRY
- Keywords
- PEPTIDE-SYNTHESIS; TURN INDUCERS; PSEUDOPROLINES; CYCLIZATION; PROTECTION; DESIGN
- Publisher's Version
- https://doi.org/10.1039/c0ob00723d
- Terms of Use/Rights Notice
- Refer to copyright notice on published article.
Creation Date: 2011-01-01 12:00:00