Enantioselective Total Synthesis of (+)-Pedrolide
Marlene Fadel1, Erick M Carreira1
1Department of Chemistry and Applied Biosciences, Laboratory of Organic Chemistry, ETH Zürich, Vladimir-Prelog-Weg 3, HCI, 8093 Zürich, Switzerland.
Abstract:
The first total synthesis of (+)-pedrolide, a tigliane-derived diterpenoid featuring an unprecedented 5-5-6-6-3 carbon skeleton, is reported. Key to the approach is the construction of the bicyclo[2.2.1]heptane core via an intramolecular cyclopentadiene-Diels-Alder cycloaddition. To this end, a norbornadiene serves as an effective surrogate for cyclopentadiene, which is unmasked under mild conditions involving a complex Diels-Alder reaction cascade. In addition, the synthesis provides a novel approach to a densely functionalized carane in an efficient and enantioselective manner.
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