Department of Chemistry , University of Adelaide , Adelaide , South Australia 5005 , Australia.
Org Lett. 2019 Oct 18;21(20):8304-8307. doi: 10.1021/acs.orglett.9b03060. Epub 2019 Oct 8.
A series of cascade reactions of -quinone methides have been developed based on the proposed biosynthesis of busseihydroquinone and parvinaphthol meroterpenoid natural products. The polycyclic framework of the most complex family members, busseihydroquinone E and parvinaphthol C, was assembled by an intramolecular [4 + 2] cycloaddition of an electron-rich chromene substrate. The resultant cyclic enol ether underwent rearrangements under acidic or oxidative conditions, which led to a new total synthesis of rhodonoid D.
基于 busseihydroquinone 和 parvinaphthol 类二萜天然产物的生物合成途径，我们开发了一系列 - 醌亚甲基的级联反应。最复杂的成员 busseihydroquinone E 和 parvinaphthol C 的多环骨架是通过富电子色烯底物的分子内[4 + 2]环加成反应构建的。所得的环状烯醇醚在酸性或氧化条件下发生重排，从而实现了 rhodonoid D 的全新全合成。
