This work was supported in part by a grant from the Institut Universitaire de France (IUF). Fellowships the French Ministry of Research and Education (V.D. and C.S.) are gratefully acknowledged.
Diversity-Oriented Synthesis of Diverse Polycyclic Scaffolds Inspired by the Logic of Sesquiterpene Lactones Biosynthesis†
Article first published online: 19 APR 2012
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 51, Issue 22, pages 5391–5394, May 29, 2012
How to Cite
Valot, G., Garcia, J., Duplan, V., Serba, C., Barluenga, S. and Winssinger, N. (2012), Diversity-Oriented Synthesis of Diverse Polycyclic Scaffolds Inspired by the Logic of Sesquiterpene Lactones Biosynthesis . Angew. Chem. Int. Ed., 51: 5391–5394. doi: 10.1002/anie.201201157
- Issue published online: 23 MAY 2012
- Article first published online: 19 APR 2012
- Manuscript Revised: 30 MAR 2012
- Manuscript Received: 11 FEB 2012
- diversity-oriented synthesis;
- natural products;
- transition metals
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.