通过分子内 Heck 反应高效不对称合成贝壳杉烷型二萜。
Efficient asymmetric synthesis of abeo-abietane-type diterpenoids by using the intramolecular Heck reaction.
机构信息
Department of Pharmaceutical Manufacturing Chemistry, 21st COE Program, Kyoto Pharmaceutical University, 1 Shichono-cho, Misasagi, Yamashina-ku, Kyoto 607-8412, Japan.
出版信息
J Org Chem. 2010 Jan 1;75(1):190-6. doi: 10.1021/jo901972b.
The synthesis of the abeo-abietane-type diterpenoids, i.e., (-)-dichroanal B, (-)-dichroanone, and taiwaniaquinone H, was achieved by using the intramolecular asymmetric Heck reaction. Our synthetic routes required fewer steps and gave a much higher overall yield and ee within shorter steps than those for racemic and antipodal forms reported to date (10, 12, and 13 steps with an overall yield of 50%, 40%, and 39%, and 94%, 98%, and 98% ee, respectively).
通过使用分子内不对称 Heck 反应，实现了 abeo-abietane 型二萜类化合物，即（-）-二氯萘 B、（-）-二氯酮和台湾醌 H 的合成。与迄今为止报道的外消旋和对映体形式相比，我们的合成路线需要的步骤更少，总收率和 ee 值更高（总收率为 50%、40%和 39%，ee 值分别为 94%、98%和 98%）。
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