title: Asymmetric synthesis of (-)-brevipolide H through cyclopropanation of the α,β-unsaturated ketone.
abstract: Brevipolides are 5,6-dihydro-γ-pyrone derivatives, first reported in 2004 as the inhibitors of the chemokine receptor CCR5 and exhibiting cytotoxicity against cancer cells. Starting from the C2 symmetric diene-diol 2, ent-brevipolide H was synthesized for the first time in 11 steps. The anti-addition of the sulfur ylide to the α,β-unsaturated enones was developed to give the key cyclopropane moiety. The synthetic (-)-brevipolide H showed an IC50 value of 7.7 μM against PC-3 cells.
authors.affiliation: Department of Chemistry, National Central University , No. 300 Jhong-Da Road, Jhong-li, Taoyuan, Taiwan 32001.
authors.forename: Jing-Wen
authors.initials: JW
authors.lastname: Lin
authors.forename: Yudhi Dwi
authors.initials: YD
authors.lastname: Kurniawan
authors.forename: Wen-Jung
authors.initials: WJ
authors.lastname: Chang
authors.forename: Wohn-Jenn
authors.initials: WJ
authors.lastname: Leu
authors.forename: She-Hung
authors.initials: SH
authors.lastname: Chan
authors.forename: Duen-Ren
authors.initials: DR
authors.lastname: Hou
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D065100:CCR5 Receptor Antagonists / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D003521:Cyclopropanes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D006801:Humans; D031331:Hyptis / Q000737:chemistry; D020128:Inhibitory Concentration 50; D007659:Ketones / Q000138:chemical synthesis / Q000737:chemistry*; D015394:Molecular Structure; D011753:Pyrones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013237:Stereoisomerism
chemical_list: D000970:Antineoplastic Agents; D065100:CCR5 Receptor Antagonists; D003521:Cyclopropanes; D007659:Ketones; D011753:Pyrones; C000592380:brevipolide H