A cascade cyclization approach to schweinfurthin B

Edward M Treadwell; Jeffrey D Neighbors; David F Wiemer

doi:10.1021/ol0266368

A cascade cyclization approach to schweinfurthin B

Org Lett. 2002 Oct 17;4(21):3639-42. doi: 10.1021/ol0266368.

Authors

Edward M Treadwell¹, Jeffrey D Neighbors, David F Wiemer

Affiliation

¹ Department of Chemistry, University of Iowa, Iowa City, Iowa 52242, USA.

PMID: 12375907
DOI: 10.1021/ol0266368

Abstract

[reaction: see text] A strategy for synthesis of the hexahydroxanthene moiety of the natural products schweinfurthin A, B, and D is described. The relative stereochemistry in the key cationic cyclization step is established through the preference of the phenylselenide substituent for an equatorial orientation.

Publication types

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

MeSH terms

Magnetic Resonance Spectroscopy
Models, Molecular
Molecular Structure
Stereoisomerism
Stilbenes / chemistry*

Substances

Stilbenes
schweinfurthin B