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.
Highlights
Hyptis brevipes Poit. is an invasive plant species belonging to the mint family Lamiaceae [1,2,3,4]
The synthesis commenced with the monoprotection of the known diene-diol ent-49 as TBS ether affording compound 50 in 76% yield, which served as an excellent strategy to direct the later cross metathesis reaction to one site of the olefin over another (Scheme 5)
The 5,6-dihydro-α-pyrone moiety is obtained via ring-closing metathesis reaction of acrylate ester 80, which in turn can be proposed from allylic alcohol 81 via Furukawa’s modified Simmons–Smith cyclopropanation (Scheme 9)
Summary
Hyptis brevipes Poit. is an invasive plant species belonging to the mint family Lamiaceae [1,2,3,4]. The synthesis commenced with the monoprotection of the known diene-diol ent-49 as TBS ether affording compound 50 in 76% yield, which served as an excellent strategy to direct the later cross metathesis reaction to one site of the olefin over another (Scheme 5). Scheme 4: Retrosynthetic analysis of brevipolide H (8) by Hou. Scheme 5: Synthesis ent-brevipolide H (ent-8) by Hou. Mohapatra’s strategy to brevipolide H (8) As part of the interest in synthesizing biologically active cyclopropane-containing natural products, Mohapatra and co-workers in 2015 started their attempt to prepare brevipolide H (8) [13].
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