Journal
ORGANIC LETTERS
Volume 11, Issue 1, Pages 89-92Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol8024617
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Funding
- Duke University, Duke Chemistry Undergraduate Summer Research Program
- NIH [PO1 CA42745]
- NIH/NCI [CA40355]
- Korean Government (MOEHRD) [KRF-2006-352-E00028]
- NATIONAL CANCER INSTITUTE [R01CA040355, P01CA042745] Funding Source: NIH RePORTER
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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.
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