Asymmetric Synthesis of (-)-Brevipolide H through Cyclopropanation of the alpha,beta-Unsaturated Ketone

作者：Lin Jing Wen; Kurniawan Yudhi Dwi; Chang Wen Jung; Leu Wohn Jenn; Chan She Hung; Hou Duen Ren^*

来源：Organic Letters, 2014, 16(20): 5328-5331.

DOI：10.1021/ol502507k

Brevipolides are 5,6-dihydro-gamma-pyrone derivatives, first reported in 2004 as the inhibitors of the chemokine receptor CCR5 and exhibiting cytotoxicity against cancer cells. Starting from the C-2 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 alpha,beta-unsaturated enones was developed to give the key cyclopropane moiety. The synthetic (-)-brevipolide H showed an IC50 value of 7.7 mu M against PC-3 cells.

• 出版日期2014-10-17
• 单位中央民族大学