Stereoselective syntheses of four diastereomers of 3,9,12-trihydroxycalamenene via a benzobicyclo[3.3.1] intermediate

Yongquan Sun; Binxun Yu; Xiaolei Wang; Shibing Tang; Xuegong She; Xinfu Pan

doi:10.1021/jo1008349

Stereoselective syntheses of four diastereomers of 3,9,12-trihydroxycalamenene via a benzobicyclo[3.3.1] intermediate

J Org Chem. 2010 Jun 18;75(12):4224-9. doi: 10.1021/jo1008349.

Authors

Yongquan Sun¹, Binxun Yu, Xiaolei Wang, Shibing Tang, Xuegong She, Xinfu Pan

Affiliation

¹ State Key Laboratory of Applied Organic Chemistry, Department of Chemistry, Lanzhou University, Lanzhou, 730000, People's Republic of China.

PMID: 20481593
DOI: 10.1021/jo1008349

Abstract

The highly stereoselective syntheses of four diastereomers of natural 3,9,12-trihydroxycalamenene are described. The syntheses highlight the utility of an unusual framework of benzobicyclo[3.3.1] lactones, which were accomplished via an intramolecular Friedel-Crafts-type Michael addition of alpha,beta-unsaturated lactones.

Publication types

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

MeSH terms

Bridged Bicyclo Compounds / chemistry*
Lactones / chemistry
Molecular Structure
Polycyclic Sesquiterpenes
Stereoisomerism
Terpenes / chemical synthesis*
Terpenes / chemistry

Substances

Bridged Bicyclo Compounds
Lactones
Polycyclic Sesquiterpenes
Terpenes
calamenene