Department of Chemistry, Indian Institute of Technology, Kanpur, 208016, India.
Org Biomol Chem. 2018 Jul 4;16(26):4793-4796. doi: 10.1039/c8ob01092g.
The first biomimetic total syntheses of chromane meroterpenoids, guadials B and C, guapsidial A and psiguajadial D have been completed. The key synthetic transformation involves an efficient and high yielding hetero-Diels-Alder reaction. The two structurally isomeric natural products, guadials B and C, were obtained from a common o-quinone methide in the separate reactions with α-pinene and β-pinene, respectively. The two regioisomeric natural products, guapsidial A and psiguajadial D, were achieved in a single chemical operation.
首次完成了色烷倍半萜类化合物瓜迪亚 B 和 C、瓜比沙醇 A 和 psiguajadial D 的仿生全合成。关键的合成转化涉及高效高产的杂 Diels-Alder 反应。两种结构异构的天然产物瓜迪亚 B 和 C 分别由α-蒎烯和β-蒎烯与一个共同的 o-醌甲醚在单独的反应中获得。两种区域异构体天然产物瓜比沙醇 A 和 psiguajadial D 则通过单一的化学反应得到。
