Stereoselective synthesis of 3-alkyl-2-aryltetrahydrofuran-4-ols: total synthesis of (+/-)-paulownin

Steven R Angle; Inchang Choi; Fook S Tham

doi:10.1021/jo800901r

Stereoselective synthesis of 3-alkyl-2-aryltetrahydrofuran-4-ols: total synthesis of (+/-)-paulownin

J Org Chem. 2008 Aug 15;73(16):6268-78. doi: 10.1021/jo800901r. Epub 2008 Jul 23.

Authors

Steven R Angle¹, Inchang Choi, Fook S Tham

Affiliation

¹ Department of Chemistry, Wright State University, Dayton, Ohio 45435, and Department of Chemistry, University of California, Riverside, California 92521, USA. [email protected]

PMID: 18646863
DOI: 10.1021/jo800901r

Abstract

A formal [3 + 2]-cycloaddition involving the Lewis acid mediated reaction of alpha-silyloxy aldehydes and styrenes to afford 3-alkyl-2-aryltetrahydrofuran-4-ols has been developed. This methodology was applied to the total synthesis of the naturally occurring furofuran lignan (+/-)-paulownin.

Publication types

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

MeSH terms

Aldehydes / chemistry
Bridged-Ring Compounds / chemical synthesis*
Bridged-Ring Compounds / chemistry
Furans / chemical synthesis*
Furans / chemistry
Lignans / chemical synthesis*
Lignans / chemistry
Magnetic Resonance Spectroscopy / methods
Stereoisomerism
Styrenes / chemistry

Substances

Aldehydes
Bridged-Ring Compounds
Furans
Lignans
Styrenes
paulownin