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
Kim, H., Wooten, C. M., Park, Y., & Hong, J. (2007). 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. Organic Letters, 9(20), 3965–3968. https://doi.org/10.1021/ol7016388
Kim, Hyoungsu, Ceshea M. Wooten, Yongho Park, and Jiyong Hong. “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.” Organic Letters 9, no. 20 (September 2007): 3965–68. https://doi.org/10.1021/ol7016388.
Kim H, Wooten CM, Park Y, Hong J. 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. Organic letters. 2007 Sep;9(20):3965–8.
Kim, Hyoungsu, et al. “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.” Organic Letters, vol. 9, no. 20, Sept. 2007, pp. 3965–68. Epmc, doi:10.1021/ol7016388.
Kim H, Wooten CM, Park Y, Hong J. 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. Organic letters. 2007 Sep;9(20):3965–3968.
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