Biomimetic Total Synthesis of (±)-Verrubenzospirolactone
Hiu C Lam1, Henry P Pepper1, Christopher J Sumby1
1Department of Chemistry, University of Adelaide, Adelaide, SA, 5005, Australia.
Abstract:
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.
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