Enantioselective total synthesis of (+)-scuteflorin A using organocatalytic asymmetric epoxidation

Christopher J Bartlett; David P Day; Yohan Chan; Steven M Allin; Michael J McKenzie; Alexandra M Z Slawin; Philip C Bulman Page

doi:10.1021/jo2021407

Enantioselective total synthesis of (+)-scuteflorin A using organocatalytic asymmetric epoxidation

J Org Chem. 2012 Jan 6;77(1):772-4. doi: 10.1021/jo2021407. Epub 2011 Dec 13.

Authors

Christopher J Bartlett¹, David P Day, Yohan Chan, Steven M Allin, Michael J McKenzie, Alexandra M Z Slawin, Philip C Bulman Page

Affiliation

¹ School of Chemistry, University of East Anglia , Norwich Research Park, Norwich, Norfolk NR4 7TJ, UK.

PMID: 22136178
DOI: 10.1021/jo2021407

Abstract

We report the first enantioselective total synthesis of (+)-scuteflorin A in 14% overall yield, employing a chiral iminium salt to effect an organocatalytic asymmetric epoxidation of xanthyletin in >99% ee as the key step.

Publication types

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

MeSH terms

Catalysis
Coumarins / chemistry*
Epoxy Compounds / chemistry*
Molecular Structure
Organic Chemistry Phenomena
Pyranocoumarins / chemical synthesis*
Pyranocoumarins / chemistry*
Stereoisomerism

Substances

Coumarins
Epoxy Compounds
Pyranocoumarins
xanthyletine
scuteflorin A