Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 134, Issue 30, Pages 12414-12417Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja305464s
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Funding
- NSFC [21072150, 30725045]
- Program for New Century Excellent Talents in University [NCET-10-0614]
- Twelfth Five-Year National Science & Technology Support Program [2012BAI29B06]
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We report the first biomimetic syntheses of (-)-gochnatiolides A-C and (-)-ainsliadimer B based on our proposed biogenetic pathway. Our synthesis features one-pot cascade transformations including Saegusa oxidation, intermolecular Diels-Alder cycloaddition, and radical-mediated allylic oxidation, which allow for the rapid generation of (-)-gochnatiolides A-C in a collective manner. We also disclose an unprecedented copper effect on the stereochemical outcome of the radical-mediated allylic oxidation. Our synthetic endeavors led to the structural reassignment of (-)-gochnatiolide B. Ultimately, a biomimetic transformation from gochnatiolide B to ainsliadimer B was achieved through a remarkable direct enone hydration.
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