Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 75, Issue 15, Pages 5392-5394Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo101016g
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Funding
- MOST [2010CB833200]
- NSFC [20872054, 20732002]
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A concise, biomimetic total synthesis of the unprecedented terpenoid skeleton (+)-chabraol has been accomplished via 6 steps from the chiral epoxide 7, involving an intramolecular Prins double cyclization to yield the bicyclo[2.2.1] core of the natural product as the key step. The absolute configuration of natural chabranol was also designated through the first asymmetric total synthesis.
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