Asymmetric synthesis of (-)-brevipolide H through cyclopropanation of the α,β-unsaturated ketone

Jing Wen Lin, Yudhi Dwi Kurniawan, Wen Jung Chang, Wohn Jenn Leu, She Hung Chan, Duen Ren Hou

Research output: Contribution to journalArticlepeer-review

16 Scopus citations

Abstract

Brevipolides are 5,6-dihydro-ã-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. (Chemical Equation Presented).

Original languageEnglish
Pages (from-to)5328-5331
Number of pages4
JournalOrganic Letters
Volume16
Issue number20
DOIs
StatePublished - 17 Oct 2014

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