Synthetic studies on antascomicin A: construction of the C18-C34 fragment |
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Authors: | Haruhiko Fuwa |
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Institution: | Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan |
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Abstract: | Stereoselective synthesis of the C18-C34 fragment of antascomicin A is described. Construction of the C27-C34 carbocycle moiety was achieved via catalytic Ferrier carbocylization and Johnson-Claisen rearrangement, which was converted to iodide 2 by use of asymmetric alkylation and Sharpless epoxidation as key transformations. Coupling of iodide 2 and sulfone 3 furnished the C18-C34 fragment. |
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Keywords: | Ferrier carbocyclization Johnson-Claisen rearrangement Asymmetric alkylation Sulfone anion coupling |
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