Diversity-Oriented Synthesis of Diverse Polycyclic Scaffolds Inspired by the Logic of Sesquiterpene Lactones Biosynthesis

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 synt...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2012-05, Vol.51 (22), p.5391-5394
Main Authors: Valot, Gaëlle, Garcia, José, Duplan, Vincent, Serba, Christelle, Barluenga, Sofia, Winssinger, Nicolas
Format: Article
Language:English
Subjects:
Analogies
Biological Products - chemical synthesis
Catalysis
Chains
Cyclization
Diphosphates
diversity-oriented synthesis
Heterocyclic Compounds - chemical synthesis
Lactones
Lactones - chemical synthesis
Metathesis
Molecular Structure
natural products
Oxygen - chemistry
Scaffolds
Sesquiterpenes - chemical synthesis
Synthesis
transition metals
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Summary: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.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201201157