Highly enantioselective total synthesis of (-)-(3'S)-Lomatin and (+)-(3'S,4'R)-trans-khellactone

Philip C Bulman Page; Louise F Appleby; David Day; Yohan Chan; Benjamin R Buckley; Steven M Allin; Michael J McKenzie

doi:10.1021/ol900444h

Highly enantioselective total synthesis of (-)-(3'S)-Lomatin and (+)-(3'S,4'R)-trans-khellactone

Org Lett. 2009 May 7;11(9):1991-3. doi: 10.1021/ol900444h.

Authors

Philip C Bulman Page¹, Louise F Appleby, David Day, Yohan Chan, Benjamin R Buckley, Steven M Allin, Michael J McKenzie

Affiliation

¹ School of Chemistry, University of East Anglia, University Plain, Norwich, Norfolk NR4 7TJ, UK. p.page@uea.ac.uk

PMID: 19354231
DOI: 10.1021/ol900444h

Abstract

Concise highly enantioselective three-step syntheses are described for (-)-(3'S)-lomatin and (+)-(3'S,4'R)-trans-khellactone from 7-hydroxycoumarin in 97% ee and in 57% and 58% overall yields, respectively, using nonaqueous enantioselective epoxidation by an iminium salt as the key step.

Publication types

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

MeSH terms

Coumarins / chemical synthesis*
Coumarins / chemistry*
Crystallography, X-Ray
Molecular Structure
Stereoisomerism
Umbelliferones / chemistry

Substances

Coumarins
Umbelliferones
lomatin
7-hydroxycoumarin
khellactone