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Synthesis of the ABCD Trioxadispiroketal Subunit of Azaspiracid-1:  An Iodoetherification−Dehydroiodination Strategy for Complex Spiroketals

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journal contribution
posted on 2007-10-11, 00:00 authored by Xiaohua Li, Jialiang Li, David R. Mootoo
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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