Angewandte Chemie - International Edition
Angewandte Chemie - International Edition
5 years ago

Biomimetic Total Synthesis of (±)-Verrubenzospirolactone

Biomimetic Total Synthesis of (±)-Verrubenzospirolactone
Henry P. Pepper, Jonathan H. George, Hiu C. Lam, Christopher J. Sumby
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. High five: A five-step total synthesis of (±)-verrubenzospirolactone (1) 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”, thus suggesting that it is likely to be non-enzymatic in nature.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/anie.201700114

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