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Rapid and Scalable Synthesis of cis ‐Fused Guaiane‐Type Sesquiterpenes
Author(s) -
Serba Christelle,
Lagoutte Roman,
Winssinger Nicolas
Publication year - 2016
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201501277
Subject(s) - bicyclic molecule , chemistry , cycloaddition , stereochemistry , substrate (aquarium) , combinatorial chemistry , scalability , organic chemistry , catalysis , computer science , database , oceanography , geology
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.