Nucleophilic addition of organozinc reagents to 2-sulfonyl cyclic ethers: stereoselective synthesis of manassantins A and B.

Journal Article (Journal Article)

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.

Full Text

Duke Authors

Cited Authors

  • Kim, H; Kasper, AC; Moon, EJ; Park, Y; Wooten, CM; Dewhirst, MW; Hong, J

Published Date

  • January 1, 2009

Published In

Volume / Issue

  • 11 / 1

Start / End Page

  • 89 - 92

PubMed ID

  • 19111058

Pubmed Central ID

  • PMC2656112

Electronic International Standard Serial Number (EISSN)

  • 1523-7052

Digital Object Identifier (DOI)

  • 10.1021/ol8024617


  • eng

Conference Location

  • United States