Application of a domino Friedel-Crafts acylation/alkylation reaction to the formal syntheses of (+/-)-taiwaniaquinol B and (+/-)-dichroanone

Shouchu Tang; Yanfen Xu; Jinmei He; Yongping He; Jiyue Zheng; Xinfu Pan; Xuegong She

doi:10.1021/ol800513v

Application of a domino Friedel-Crafts acylation/alkylation reaction to the formal syntheses of (+/-)-taiwaniaquinol B and (+/-)-dichroanone

Org Lett. 2008 May 1;10(9):1855-8. doi: 10.1021/ol800513v. Epub 2008 Apr 8.

Authors

Shouchu Tang¹, Yanfen Xu, Jinmei He, Yongping He, Jiyue Zheng, Xinfu Pan, Xuegong She

Affiliation

¹ Department of Chemistry, State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, PR China.

PMID: 18393520
DOI: 10.1021/ol800513v

Abstract

An efficient acid-promoted domino Friedel-Crafts (FC) acylation/alkylation reaction has been developed for the construction of the core 6,5,6-ABC tricyclic skeleton of taiwaniaquinoids. The formal total syntheses of diterpenoids (+/-)-taiwaniaquinol B and (+/-)-dichroanone based on this strategy have been achieved.

Publication types

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

MeSH terms

Acylation
Alkylation
Diterpenes / chemical synthesis*
Diterpenes / chemistry
Plant Preparations / chemistry

Substances

Diterpenes
Plant Preparations
dichroanone
taiwaniaquinol B