119. Rapid and Scalable Synthesis of cis-Fused Guaiane-Type Sesquiterpenes
     C. Serba, R. Lagoutte, N. Winssinger
     Eur. J. Org. Chem. 2016, 644-646

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.

DOI : 10.1002/ejoc.201501277 

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