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).
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Kurniawan, Y. D. (Contributor), Chang, W. (Contributor), Leu, W. (Contributor), Chan, S. (Contributor), Lin, J. (Contributor) & Hou, D. (Contributor), The Cambridge Structural Database, 17 Oct 2014