An efficient total synthesis of (+/-)-stemonamine

Yu-Ming Zhao; Peiming Gu; Yong-Qiang Tu; Chun-An Fan; Qingwei Zhang

doi:10.1021/ol800433r

An efficient total synthesis of (+/-)-stemonamine

Org Lett. 2008 May 1;10(9):1763-6. doi: 10.1021/ol800433r. Epub 2008 Mar 26.

Authors

Yu-Ming Zhao¹, Peiming Gu, Yong-Qiang Tu, Chun-An Fan, Qingwei Zhang

Affiliation

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

PMID: 18363326
DOI: 10.1021/ol800433r

Abstract

An efficient first approach to the Stemona alkaloid (+/-)-Stemonamine has been developed on the basis of a key TiCl4 promoted tandem Semipinacol rearrangement/Schmidt reaction and a Dieckmann condensation reaction.

Publication types

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

MeSH terms

4-Butyrolactone / analogs & derivatives*
4-Butyrolactone / chemical synthesis
4-Butyrolactone / chemistry
Alkaloids / chemical synthesis*
Alkaloids / chemistry
Azepines / chemical synthesis*
Azepines / chemistry
Molecular Structure
Stemonaceae / chemistry
Stereoisomerism
Titanium / chemistry*

Substances

Alkaloids
Azepines
stemonamine
titanium tetrachloride
Titanium
4-Butyrolactone