Synthesis of neolamellarin A, an inhibitor of hypoxia-inducible factor-1.
Neolamellarin A, a metabolite isolated from the sponge Dendrilla nigra, was found to inhibit hypoxia-inducible factor-1 (HIF-1) activation by 26% at 10 microM concentration and inhibition of HIF-1 has become a major antitumor molecular target. Herein the first synthesis of neolamellarin A is described. The synthetic strategy features the condensation of vinylogous amide with aminomalonate to construct the 3,4-bis(4-methoxyphenyl)-1H-pyrrole core and the subsequent acylation and deprotection rendered the target compound in 18% over all yield.
Version: za2963e q8za0 q8zb9 q8zcd q8zd0 q8ze3 q8zfe q8zg9