Strategies for the synthesis of brevipolides

Abstract

In recent years fifteen 5,6-dihydro-α-pyrone derivatives, bearing either a distinctive cyclopropane or furan ring and named brevipolides A–O (1–15), have been isolated from the invasive plant Hyptis brevipes Poit. Their fascinating structural features, and the potent biological activities, including cytotoxicity against an array of human cancer cell lines and inhibition of the chemokine receptor CCR5, make them attractive synthetic targets. This review article highlights the recent synthetic methodologies and briefly summarizes their biological activities.

Stereoselective Total Synthesis of (+)-Brevipolide H from d-Galactal

“…4 Given their novel structural features and promising biological activities in conjunction with their potential medicinal application, brevipolides have prompted several synthetic groups to target their total synthesis. 5 6 7 8 9 To date, two total syntheses of brevipolide H ( 8 ) 6 7 and two syntheses for its derivative 8 and fragment 9 have been reported in the literature. Pioneering synthetic studies were conducted by Hou 6 and Kumaraswamy, 8 individually.…”