Catalytic Asymmetric Synthesis of Biologically Important Molecules

生物重要分子的催化不对称合成

• 批准号: 02453137
• 负责人: SHIBASAKI Masakatsu
• 金额: $ 3.71万
• 依托单位: Hokkaido University
• 依托单位国家: 日本
• 项目类别: Grant-in-Aid for General Scientific Research (B)
• 财政年份: 1990
• 资助国家: 日本
• 起止时间: 1990 至 1991
• 项目状态: 已结题
• 来源: https://kaken.nii.ac.jp/en/grant/KAKENHI-PROJECT-02453137/
• 关键词: Heck Reaction; Catalytic Asymmetric Synthesis; Decalin Derivatives; Hydrindan Derivatives; Capnellenol; Marine Natural Product; カプネレノ-ル; 不斉ヘック反応; 不斉πーアリルパラジウム; カプネランアルコ-ル; アザディラクチン

Previously we developed an asymmetric Heck reaction, in which the cis-decalin derivative was obtained in 45% ee. Now we have succeeded in improving the above-mentioned asymmetric Heck reaction as shown below.Furthermore, we have accomplished a catalytic asymmetric synthesis of capnellenols 5 and 6 by utilizing an asymmetric Heck reaction. On the other hand, the cis-decalin derivative 7 has been found to be synthesized in 83% ee through the pi-allylpalladium intermediate.

以前我们开发了一个不对称Heck反应，其中在45%的ee中得到顺式十氢化萘衍生物。现在我们成功地改进了上述不对称Heck反应，如下图所示。此外，我们还利用不对称Heck反应完成了催化不对称合成辣椒烯醇5和6。另一方面，通过pi-烯基钯中间体，以83%的ee合成了顺式十氢化萘衍生物7。

项目成果

Yoshihiro Sato: "On the Role of Silver Salts in Asymmetric Heckーtype Reaction.A Greathy Improved Catahytic Asymmetric Synthesis of Cis Decalin Deriratiues" Chemistry Letters. 1953-1954 (1990)

Yoshihiro Sato：“关于银盐在不对称 Heck 型反应中的作用。顺式十氢化萘衍生物的催化不对称合成的极大改进”化学快报 1953-1954（1990 年）。

Yoshihiro Soto: "On the Role of Silver Salts in Asymmetric Heck-type Reaction. A Greatly Improved Catalytic Asymmetric Synthesis of cis-Decalin Derivatives" Chemistry Letters. 56. 1953-1954 (1990)

Yoshihiro Soto：“论银盐在不对称 Heck 型反应中的作用。顺式十氢萘衍生物的极大改进的催化不对称合成”化学快报。

Katsuji Kagechika: "Asymmetric Heck Reaction. A Catalytic Asymmectric Synthesis of the Key Intermediate for DELTA^<9(12)>-Caonellene-3beta, 8beta, 10alpha-triol and DELTA^<9(12)>-Caonellene-3bata, 8beta, 10alpha, 14-tetrol" 4093-4094 (1991)

Katsuji Kagechika：“不对称 Heck 反应。DELTA^<9(12)>-Caonellene-3beta、8beta、10alpha-三醇和 DELTA^<9(12)>-Caonellene-3bata、8beta 关键中间体的催化不对称合成

Yoshihiro Sato: "On the Role of Siluer Salts in Asymmetric Heckーtype Reaction.A Greatly Improued catalytic.Asymmetric Synthesis of c<is>___ーーDecalin Decuvetiucs" Chemistry Letters. 1953-1954 (1990)

Yoshihiro Sato：“论硅盐在不对称 Heck 型反应中的作用。顺式___-十氢萘 Decuvetiucs 的催化不对称合成的极大改进”化学快报 1953-1954（1990 年）。

Katsuji Kagechika: "Asymmetric Heck Reaction.A Catalytic Asymmetric Synthesis of the Key Intirmediate for DELTA^<9(12)>-Capnellener 3beta,8beta,10alpha-triol and DELTA9^<9(12)>-Capnel〓ne-3beta,8beta,10alpha,14-litrol." The Journal of Organic Chemistry. 56

Katsuji Kagechika：“不对称 Heck 反应。DELTA^<9(12)>-Capnellener 3beta,8beta,10alpha-三醇和 DELTA9^<9(12)>-Capnel〓ne-3beta 关键中间体的催化不对称合成， 8beta,10alpha,14-litrol。”有机化学杂志。56