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Total Synthesis and Determination of the Absolute Configuration of Berkeleylactone I
Sudip Mandal1, Dora Mahananda1, Dileep Paladugu1
1Department of Chemical Sciences, Indian Institute of Science Education and Research Berhampur, Transit Campus, Government ITI Building, NH 59, Engineering School Road, Ganjam District, Berhampur 760 010, Odisha, India.
Abstract:
Herein, we report the first total synthesis of berkeleylactone I and its 12S diastereomer. Consequently, this chemical synthesis allowed us to establish the unknown absolute stereochemistry at the C-12 center as 12R, which was unidentified by the isolation group. This synthetic approach includes several critical reactions, such as the Sharpless asymmetric dihydroxylation, Baran's Ni-catalyzed alkyl-alkyl cross-coupling reaction, Brown allylation, Mitsunobu reaction, and ring-closing metathesis, as key steps.
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