Total synthesis of (+)-tedanolide |
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Authors: | Smith Amos B Lee Dongjoo |
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Affiliation: | Department of Chemistry, Laboratory for Research on the Structure of Matter, and Monell Chemical Senses Center, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323, USA. smithab@sas.upenn.edu |
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Abstract: | A convergent, stereocontrolled total synthesis of (+)-tedanolide (1), an architecturally complex marine antitumor macrolide, has been achieved in 31 steps (longest linear sequence). Highlights of the synthesis comprise a highly efficient dithiane union, followed by an Evans-Tishchenko "oxidation" to enable formation of the seco-ester in the presence of an oxidatively labile dithiane, a highly refined protecting group strategy, and a chemo- and stereoselective epoxidation at C(18,19). |
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