Stereoselective syntheses of (+/-)-komaroviquinone and (+/-)-faveline methyl ether through intramolecular Heck reaction

Sujaya Sengupta; Michael G B Drew; Ranjan Mukhopadhyay; Basudeb Achari; Asish Kr Banerjee

doi:10.1021/jo051082i

Stereoselective syntheses of (+/-)-komaroviquinone and (+/-)-faveline methyl ether through intramolecular Heck reaction

J Org Chem. 2005 Sep 16;70(19):7694-700. doi: 10.1021/jo051082i.

Authors

Sujaya Sengupta¹, Michael G B Drew, Ranjan Mukhopadhyay, Basudeb Achari, Asish Kr Banerjee

Affiliation

¹ Medicinal Chemistry Division, Indian Institute of Chemical Biology, 4 Raja S. C. Mullick Road, Kolkata-700 032, India.

PMID: 16149801
DOI: 10.1021/jo051082i

Abstract

[reaction: see text] An efficient, flexible, and stereoselective convergent route for constructing the trans-10-hydroxy-1,1-dimethyloctahydrodibenzo[a,d]cyclohepten-7-ones (5a-c) was achieved via intramolecular Heck reaction. This strategy has been successfully implemented for the syntheses of (+/-)-komaroviquinone (3) through (+/-)-coulterone dimethyl ether (5c) and (+/-)-faveline methyl ether (1a).

Publication types

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

MeSH terms

Antineoplastic Agents, Phytogenic / chemical synthesis*
Diterpenes / chemical synthesis*
Quinones / chemical synthesis*

Substances

Antineoplastic Agents, Phytogenic
Diterpenes
Quinones
komaroviquinone