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- Title
Synthesis of cis-enamide macrocycles via ring-closing metathesis.
- Authors
Ramírez, Moisés; Ochoa-Terán, Adrián; Somanathan, Ratnasamy; Aguirre, Gerardo
- Abstract
Herein we report the synthesis of 13-, 14- and 15-membered cyclic lactams, using Grubbs' RCM method in 25, 52 and 46% yields respectively. The cis-enamide functional group was successfully introduced into these cyclic lactams by syn sulfoxide elimination The synthetic cyclic lactams resemble natural cyclic peptides. Our synthetic methodology provides a simple route to making medium-sized cyclic lactams that could be used as models to mimic the β-turn in natural proteins, an important marker in understanding their biological activity.
- Subjects
MACROCYCLIC compound synthesis; METATHESIS reactions; RING formation (Chemistry); CHEMICAL yield; LACTAM derivatives
- Publication
ARKIVOC: Online Journal of Organic Chemistry, 2017, Vol 2017, p194
- ISSN
1551-7004
- Publication type
Article
- DOI
10.3998/ark.5550190.0018.400