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Molecules  2011 

Synthesis of Key Fragments of Amphidinolide Q — A Cytotoxic 12-membered Macrolide

DOI: 10.3390/molecules16075422

Keywords: amphidinolide Q, Amphidinium sp., macrolide synthesis, cytotoxic marine natural product

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Abstract:

b-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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