Synthesis of C1−C9 and C10−C21 Fragments of (−)‐Dolabriferol,Asian Journal of Organic Chemistry

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Synthesis of C1−C9 and C10−C21 Fragments of (−)‐Dolabriferol
Asian Journal of Organic Chemistry ( IF 2.8 ) Pub Date : 2020-05-20 , DOI: 10.1002/ajoc.202000255
Anandaraju Bandaru ₁ , Debjani Si ₁ , Krishna P. Kaliappan ₁

Affiliation

Our efforts on the synthesis of C₁−C₉ and C₁₀−C₂₁ subunits of dolabriferol, a non‐contiguous polypropionate marine natural product, from a common intermediate using two non‐aldol variants is reported. i) Shimizu reaction, a Pd(0) mediated stereoselective epoxy‐ring opening of alkenyl oxiranes, has been employed for the stereoselective installation of methyl groups at C₄ and C₁₃ and ii) Bode's protocol, a NHC‐mediated reaction on β‐epoxy aldehydes, has been utilized for stereoselective construction of methyl and hydroxyl groups in anti‐fashion at C₆−C₇ and C₁₅−C₁₆ in the natural product.

中文翻译：

（-）-二十碳四烯醇的C1-C9和C10-C21片段的合成

据报道，我们使用两种非醛醇变体从共同的中间体合成多布拉夫罗酚的C ₁ -C ₉和C ₁₀ -C ₂₁亚基，这是一种不连续的聚丙烯酸酯海洋天然产物。i）清水反应（Pd（0）介导的烯基环氧乙烷的立体选择性环氧环开环）已用于在C ₄和C ₁₃处进行甲基的立体选择性安装，ii）Bode方案，NHC介导的β-上的反应环氧醛已被用于在C ₆ -C ₇和C ₁₅ -C _16的反时尚立体选择性地构建甲基和羟基在天然产物中。

更新日期：2020-07-08

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