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  • Title: Synthesis of key fragments of amphidinolide Q--a cytotoxic 12-membered macrolide.
    Author: Kawa K, Hara A, Ishikawa Y, Nishiyama S.
    Journal: Molecules; 2011 Jun 27; 16(7):5422-36. PubMed ID: 21709623.
    Abstract:
    β-hydroxy aldehyde and alkyl ketone moieties were effectively synthesized as key intermediates of amphidinolide Q, a cytotoxic macrolide from the cultured dinoflagellate Amphidinium sp.. The asymmetric center of the former derivative was produced by Sharpless asymmetric epoxidation, followed by E-selective 1,4-addition to give the sp² methyl group. Derivatization of the L-ascorbic acid derivative by Evans asymmetric alkylation and Peterson olefination provided the latter intermediate. The coupling reaction of the segments was examined.
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