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.
Highlights
Amphidinolide Q (1, Scheme 1) is a member of the cytotoxic macrolide family isolated from the cultured dinoflagellate Amphidinium sp., and its absolute stereostructure was chemically determined by Kobayashi and co-workers [1,2]
1 was synthesized by Kobayashi’s group in 2009 [3], further increases in synthetic efficiency and examination of related substances based on new synthetic approaches are Molecules 2011, 16 required to explain the detailed mode of action of 1 by structure-activity relationship studies, and to develop new bioactive substances superior to the mother macrolide
We describe an efficient method for synthesis of segments 2 and 3, which will be important intermediates for the construction of 1
Summary
Amphidinolide Q (1, Scheme 1) is a member of the cytotoxic macrolide family isolated from the cultured dinoflagellate Amphidinium sp., and its absolute stereostructure was chemically determined by Kobayashi and co-workers [1,2].
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