Stereoselective synthesis of tetrahydrofuran lignans via BF(3) x OEt(2)-promoted reductive deoxygenation/epimerization of cyclic hemiketal: synthesis of (-)-odoratisol C, (-)-futokadsurin A, (-)-veraguensin, (+)-fragransin A(2), (+)-galbelgin, and (+)-talaumidin

Hyoungsu Kim; Ceshea M Wooten; Yongho Park; Jiyong Hong

doi:10.1021/ol7016388

Stereoselective synthesis of tetrahydrofuran lignans via BF(3) x OEt(2)-promoted reductive deoxygenation/epimerization of cyclic hemiketal: synthesis of (-)-odoratisol C, (-)-futokadsurin A, (-)-veraguensin, (+)-fragransin A(2), (+)-galbelgin, and (+)-talaumidin

Org Lett. 2007 Sep 27;9(20):3965-8. doi: 10.1021/ol7016388. Epub 2007 Sep 1.

Authors

Hyoungsu Kim¹, Ceshea M Wooten, Yongho Park, Jiyong Hong

Affiliation

¹ Department of Chemistry, Duke University, Durham, North Carolina 27708, USA.

PMID: 17764190
DOI: 10.1021/ol7016388

Abstract

A versatile route to the synthesis of 2,5-diaryl-3,4-dimethyltetrahydrofuran lignans, (-)-odoratisol C (1), (-)-futokadsurin A (2), (-)-veraguensin (3), (+)-fragransin A2 (4), (+)-galbelgin (5), and (+)-talaumidin (6), is described. Central to the synthesis of the lignans is BF(3) x OEt(2)-promoted deoxygenation/epimerization of the hemiketal 9a followed by stereoselective reduction of the oxocarbenium ion intermediates 8a,b.

Publication types

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

MeSH terms

Bromine Compounds / chemistry*
Cyclization
Ether / chemistry*
Fluorine Compounds / chemistry*
Furans / chemistry*
Hydrogen / chemistry*
Lignans / chemical synthesis*
Lignans / chemistry
Molecular Structure
Oxidation-Reduction
Stereoisomerism

Substances

Bromine Compounds
Fluorine Compounds
Furans
Lignans
Ether
Hydrogen
bromine trifluoride