Syntheses of Cerulenin and Its Analogs. II. Synthesis and Biological Activity of dl-Carbacerulenin, a Carbocyclic Analog of Cerulenin

Abstract

2, 3-Epoxy-4-hydroxy-4-((E, E)-3, 6-octadienyl)cyclopentanone (dl-carbacerulenin 5) was synthesized via the epoxyketones 15a and 15b as a mimic of the active form of the antibiotics cerulenin 1, a potent inhibitor of fatty acid synthetase (FAS). The monobenzyl ethers (12 and 13), synthetic intermediates of 15, were prepared by direct benzylation of the epoxycyclopentene (7). Inhibitory activity of synthesized 5 toward yeast FAS was less than that of cerulenin by a factor of 1000.