Asymmetric total synthesis and revision of the absolute configuration of 4-keto-clonostachydiol

Junjie Han; Yingpeng Su; Tuo Jiang; Yanfen Xu; Xing Huo; Xuegong She; Xinfu Pan

doi:10.1021/jo900370a

Asymmetric total synthesis and revision of the absolute configuration of 4-keto-clonostachydiol

J Org Chem. 2009 May 15;74(10):3930-2. doi: 10.1021/jo900370a.

Authors

Junjie Han¹, Yingpeng Su, Tuo Jiang, Yanfen Xu, Xing Huo, Xuegong She, Xinfu Pan

Affiliation

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

PMID: 19382764
DOI: 10.1021/jo900370a

Abstract

The first total synthesis of the 14-membered natural macrocyclic bislactone 4-keto-clonostachydiol, along with its enantiomer, has been accomplished in 13 steps with overall yields of 8.4% and 8.0%, respectively. The absolute configuration of 4-keto-clonostachydiol 1 has been revised as (5S,10S,13S).

Publication types

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

MeSH terms

Epoxy Compounds / chemistry
Lactones / chemical synthesis*
Lactones / chemistry
Stereoisomerism
Substrate Specificity

Substances

4-keto-clonostachydiol
Epoxy Compounds
Lactones
propylene oxide