Multiple chirality transfers in the enantioselective synthesis of 11-O-debenzoyltashironin. Chiroptical analysis of the key cascade |
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| Authors: | Alessandra Polara Samuel J Danishefsky |
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| Institution: | a Department of Chemistry, Columbia University, 3000 Broadway, New York, NY 10027, USA
b Laboratory for Bioorganic Chemistry, Sloan-Kettering Institute for Cancer Research, 1275 York Avenue, New York, NY 10065, USA |
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| Abstract: | The mechanism of the cascade oxidative dearomatization-transannular Diels-Alder was investigated in the context of an asymmetric route to (−)-11-O-debenzoyltashironin. Although the oxidative dearomatization provides two acetal intermediates, the transannular Diels-Alder proceeds spontaneously from only one of the acetal isomers. Access to enantioenriched tetracyclic adduct was gained through the use of optically active allene. |
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