Synthesis of the ABCD trioxadispiroketal subunit of azaspiracid-1: an iodoetherification-dehydroiodination strategy for complex spiroketals |
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Authors: | Li Xiaohua Li Jialiang Mootoo David R |
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Institution: | Department of Chemistry, Hunter College, 695 Park Avenue, New York, New York 10065, USA. |
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Abstract: | An unusual spiroketalization strategy in which a hydroxyalkene serves as a precursor to a cyclic enol ether was applied to the synthesis of the ABCD trioxadispiroketal subunit of azaspiracid-1. The trioxadispiroketal product, which represents a double anomeric effect, was obtained as a single trioxadispiroketal diastereomer. A key ploy in the synthesis of the CD segment was the use of a cyclopropane as a synthon for the C-14 methyl group. |
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