Total synthesis of (-)-jiadifenin

Yang Yang; Xingnian Fu; Jianwei Chen; Hongbin Zhai

doi:10.1002/anie.201203176

Total synthesis of (-)-jiadifenin

Angew Chem Int Ed Engl. 2012 Sep 24;51(39):9825-8. doi: 10.1002/anie.201203176. Epub 2012 Aug 24.

Authors

Yang Yang¹, Xingnian Fu, Jianwei Chen, Hongbin Zhai

Affiliation

¹ Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, China.

PMID: 22926836
DOI: 10.1002/anie.201203176

Abstract

As easy as ABCD: (-)-Jiadifenin was synthesized in eighteen reaction steps from 1-[(E)-(4'-bromo-2'-butenyl)oxy]-4-methoxybenzene. Key features of this synthesis include: 1) Ireland-Claisen rearrangement to produce the two contiguous quaternary centers at C5 and C6 simultaneously, 2) intramolecular Pauson-Khand reaction (IMPKR) to concurrently construct the A and B rings, and 3) [2+2] photo-cycloaddition to generate the all-carbon quaternary center at C9.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Cycloaddition Reaction
Illicium / chemistry*
Models, Molecular
Sesquiterpenes / chemical synthesis*
Sesquiterpenes / chemistry
Stereoisomerism

Substances

Sesquiterpenes
jiadifenin