Benzoylureas as removable cis amide inducers: synthesis of cyclic amides via ring closing metathesis (RCM)
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
Rights Notice
Refer to copyright notice on published article.


Creation Date: 2011-01-01 12:00:00
Last Modified: 0001-01-01 12:00:00
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