Skip to main content
Journal cover image

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.

Publication ,  Journal Article
Kim, H; Wooten, CM; Park, Y; Hong, J
Published in: Organic letters
September 2007

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.

Duke Scholars

Published In

Organic letters

DOI

EISSN

1523-7052

ISSN

1523-7060

Publication Date

September 2007

Volume

9

Issue

20

Start / End Page

3965 / 3968

Related Subject Headings

  • Stereoisomerism
  • Oxidation-Reduction
  • Organic Chemistry
  • Molecular Structure
  • Lignans
  • Hydrogen
  • Furans
  • Fluorine Compounds
  • Ether
  • Cyclization
 

Citation

APA
Chicago
ICMJE
MLA
NLM
Journal cover image

Published In

Organic letters

DOI

EISSN

1523-7052

ISSN

1523-7060

Publication Date

September 2007

Volume

9

Issue

20

Start / End Page

3965 / 3968

Related Subject Headings

  • Stereoisomerism
  • Oxidation-Reduction
  • Organic Chemistry
  • Molecular Structure
  • Lignans
  • Hydrogen
  • Furans
  • Fluorine Compounds
  • Ether
  • Cyclization