期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 56, 期 29, 页码 8532-8535出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201700114
关键词
biomimetic synthesis; cycloaddition; natural products; terpenoids; total synthesis
资金
- Australian Research Council [DP160103393]
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 degrees 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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