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- Title
Rapid and Scalable Synthesis of cis-Fused Guaiane-Type Sesquiterpenes.
- Authors
Serba, Christelle; Lagoutte, Roman; Winssinger, Nicolas
- Abstract
Sesquiterpenes have been a rich source of bioactive compounds and have inspired innovative methodological developments. Herein we report a rapid and scalable synthesis of a substrate for a 4+3 cycloaddition in order to access the cis-fused bicyclic system of the guaianes. We further show diverse and efficient functionalizations of the bicyclic system. The relative stereochemistry was assigned based on the crystal structure of a key product.
- Subjects
SESQUITERPENES; CHEMICAL synthesis; BIOACTIVE compounds; RING formation (Chemistry); RING formation (Chemistry) kinetics; STEREOCHEMISTRY; STEREOSELECTIVE reactions; MATHEMATICAL models
- Publication
European Journal of Organic Chemistry, 2016, Vol 2016, Issue 4, p644
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201501277