Publications [#168950] of Mark W. Dewhirst

Papers Published

1. H Kim, AC Kasper, EJ Moon, Y Park, CM Wooten, MW Dewhirst, J Hong, Nucleophilic addition of organozinc reagents to 2-sulfonyl cyclic ethers: stereoselective synthesis of manassantins A and B., Organic letters, United States, vol. 11 no. 1 (January, 2009), pp. 89-92, ISSN 1523-7052
   (last updated on 2009/12/31)

   Abstract:
   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.

   Keywords:
   Ethers, Cyclic • Furans • Hypoxia-Inducible Factor 1 • Lignans • Molecular Conformation • Organometallic Compounds • Stereoisomerism • Sulfones • Zinc • antagonists & inhibitors • chemical synthesis* • chemistry • chemistry* • pharmacology