Department of Chemistry, University of Adelaide, Adelaide, SA, 5005, Australia.
Angew Chem Int Ed Engl. 2017 Jul 10;56(29):8532-8535. doi: 10.1002/anie.201700114. Epub 2017 Feb 22.
A five-step total synthesis of (±)-verrubenzospirolactone has been achieved using a biomimetic, intramolecular Diels-Alder reaction of a 2H-chromene to form two rings and four stereocenters in the final step. This Diels-Alder reaction occurs spontaneously at 30 °C "on-water", and thus suggests that it is likely to be non-enzymatic in nature. The structure of (±)-verrubenzospirolactone was also used to inspire a quadruple cascade reaction to generate seven stereocenters, four rings, three C-C bonds, and two C-O bonds in one step.
（±）-verrubenzospirolactone 的五步全合成已通过仿生、2H-色烯的分子内 Diels-Alder 反应实现，该反应在最后一步形成两个环和四个手性中心。该 Diels-Alder 反应在 30°C 的“水上”自发进行，因此推测其可能是非酶促的。（±）-verrubenzospirolactone 的结构也被用来启发四重级联反应，一步生成七个手性中心、四个环、三个 C-C 键和两个 C-O 键。
