Nucleophilic addition of organozinc reagents to 2-sulfonyl cyclic ethers: stereoselective synthesis of manassantins A and B.
Publication
, Journal Article
Kim, H; Kasper, AC; Moon, EJ; Park, Y; Wooten, CM; Dewhirst, MW; Hong, J
Published in: Org Lett
January 1, 2009
A convergent route to the synthesis of manassantins A and B, potent inhibitors of HIF-1, is described. Central to the synthesis is a stereoselective addition of an organozinc reagent to a 2-benzenesulfonyl cyclic ether to achieve the 2,3-cis-3,4-trans-4,5-cis-tetrahydrofuran of the natural products. Preliminary structure-activity relationships suggested that the (R)-configuration at C-7 and C-7''' is not critical for HIF-1 inhibition. In addition, the hydroxyl group at C-7 and C-7''' can be replaced with a carbonyl group without loss of activity.
Duke Scholars
Published In
Org Lett
DOI
EISSN
1523-7052
Publication Date
January 1, 2009
Volume
11
Issue
1
Start / End Page
89 / 92
Location
United States
Related Subject Headings
- Zinc
- Sulfones
- Stereoisomerism
- Organometallic Compounds
- Organic Chemistry
- Molecular Conformation
- Lignans
- Hypoxia-Inducible Factor 1
- Furans
- Ethers, Cyclic
Citation
APA
Chicago
ICMJE
MLA
NLM
Kim, H., Kasper, A. C., Moon, E. J., Park, Y., Wooten, C. M., Dewhirst, M. W., & Hong, J. (2009). Nucleophilic addition of organozinc reagents to 2-sulfonyl cyclic ethers: stereoselective synthesis of manassantins A and B. Org Lett, 11(1), 89–92. https://doi.org/10.1021/ol8024617
Kim, Hyoungsu, Amanda C. Kasper, Eui Jung Moon, Yongho Park, Ceshea M. Wooten, Mark W. Dewhirst, and Jiyong Hong. “Nucleophilic addition of organozinc reagents to 2-sulfonyl cyclic ethers: stereoselective synthesis of manassantins A and B.” Org Lett 11, no. 1 (January 1, 2009): 89–92. https://doi.org/10.1021/ol8024617.
Kim H, Kasper AC, Moon EJ, Park Y, Wooten CM, Dewhirst MW, et al. Nucleophilic addition of organozinc reagents to 2-sulfonyl cyclic ethers: stereoselective synthesis of manassantins A and B. Org Lett. 2009 Jan 1;11(1):89–92.
Kim, Hyoungsu, et al. “Nucleophilic addition of organozinc reagents to 2-sulfonyl cyclic ethers: stereoselective synthesis of manassantins A and B.” Org Lett, vol. 11, no. 1, Jan. 2009, pp. 89–92. Pubmed, doi:10.1021/ol8024617.
Kim H, Kasper AC, Moon EJ, Park Y, Wooten CM, Dewhirst MW, Hong J. Nucleophilic addition of organozinc reagents to 2-sulfonyl cyclic ethers: stereoselective synthesis of manassantins A and B. Org Lett. 2009 Jan 1;11(1):89–92.
Published In
Org Lett
DOI
EISSN
1523-7052
Publication Date
January 1, 2009
Volume
11
Issue
1
Start / End Page
89 / 92
Location
United States
Related Subject Headings
- Zinc
- Sulfones
- Stereoisomerism
- Organometallic Compounds
- Organic Chemistry
- Molecular Conformation
- Lignans
- Hypoxia-Inducible Factor 1
- Furans
- Ethers, Cyclic