Total synthesis of jiadifenolide.

Abstract

As a potent neurotrophic agent, the sesquiterpenoid jiadifenolide represents a valuable small-molecule lead for the potential therapeutic treatment of neurodegenerative diseases. A stereocontrolled total synthesis of this densely functionalized natural product is reported, central to which is an adventurous samarium-mediated cyclization reaction to establish the tricyclic core and the adjacent C5 and C6 quaternary stereocenters.

• Authors: Ian Paterson, Mengyang Xuan, Stephen M Dalby
• Journal: Angewandte Chemie (International ed. in English) (Angew Chem Int Ed Engl) Vol. 53 Issue 28 Pg. 7286-9 (Jul 07 2014) ISSN: 1521-3773 [Electronic] Germany
• PMID: 24861364 (Publication Type: Journal Article)
• Copyright: © 2014 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.

Chemical References

• Sesquiterpenes
• Vinyl Compounds
• jiadifenolide

Topics

• Crystallography, X-Ray
• Cyclization
• Molecular Structure
• Oxidation-Reduction
• Sesquiterpenes (chemical synthesis, chemistry)
• Stereoisomerism
• Vinyl Compounds (chemistry)