Premium
Diversity‐Oriented Synthesis of Diverse Polycyclic Scaffolds Inspired by the Logic of Sesquiterpene Lactones Biosynthesis
Author(s) -
Valot Gaëlle,
Garcia José,
Duplan Vincent,
Serba Christelle,
Barluenga Sofia,
Winssinger Nicolas
Publication year - 2012
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201201157
Subject(s) - metathesis , analogy , sesquiterpene , biosynthesis , chemistry , stereochemistry , combinatorial chemistry , organic chemistry , philosophy , linguistics , polymerization , enzyme , polymer
Natural selection : An acyclic chain containing an ene‐yne‐ene motif, in analogy to farnesyl diphosphate, was cyclized to obtain six distinct scaffolds using different transition‐metal catalysts (see scheme). Notably, the guaianolide framework was accessed through enynene metathesis enabling the synthesis of three natural products.