Frutescone A–G, Tasmanone-Based Meroterpenoids from the aerial parts of Baeckea frutescens

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• 作者：Ji-Qin Hou ; Cui Guo ; Jian-Juan Zhao ; Qi-Wei He ; Bao-Bao Zhang ; Hao Wang
• 刊名：Journal of Organic Chemistry
• 出版年：2017
• 出版时间：February 3, 2017
• 年：2017
• 卷：82
• 期：3
• 页码：1448-1457
• 全文大小：653K
• ISSN：1520-6904

文摘

Frutescone A–G [(1–6), (+)-7, (−)-7], a new group of naturally occurring tasmanone-based meroterpenoids, were isolated from the aerial parts of Baeckea frutescens L. Compounds 1 and 4 featured a rare carbon skeleton with an unprecedented oxa-spiro[5.8] tetradecadiene ring system, existing as two favored equilibrating conformers in CDCl₃ solution, identified by variable-temperature NMR. The regioselective syntheses of 4–7 were achieved in a concise manner by a biomimetically inspired key hetero-Diels–Alder reaction “on water”. Compounds 1, 4, and 5 exhibited moderate cytotoxicities in vitro.