合成 Amphidinolide Q 的关键片段——一种细胞毒性的 12 元大环内酯。
Synthesis of key fragments of amphidinolide Q--a cytotoxic 12-membered macrolide.
机构信息
Department of Chemistry, Faculty of Science and Technology, Keio University, Hiyoshi 3-14-1, Kohoku-ku, Yokohama 223-8522, Japan.
出版信息
Molecules. 2011 Jun 27;16(7):5422-36. doi: 10.3390/molecules16075422.
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.
β-羟基醛和烷基酮部分被有效地合成，作为 Amphidinolide Q 的关键中间体，Amphidinium sp. 培养的细胞毒大环内酯。前者的不对称中心是由 Sharpless 不对称环氧化产生的，然后通过 E-选择性 1,4-加成得到 sp² 甲基。L-抗坏血酸衍生物的衍生化通过 Evans 不对称烷基化和 Peterson 烯烃化提供了后者的中间体。对片段的偶联反应进行了考察。
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