Synthetic approach directed toward the determination of the stereochemistry of scarce natural products with potent antimitotic or cytotoxic activity

用于测定具有有效抗有丝分裂或细胞毒性活性的稀有天然产物的立体化学的合成方法

• 批准号: 24658105
• 负责人: KUWAHARA Shigefumi
• 金额: $ 2.58万
• 依托单位: Tohoku University
• 依托单位国家: 日本
• 项目类别: Grant-in-Aid for Challenging Exploratory Research
• 财政年份: 2012
• 资助国家: 日本
• 起止时间: 2012-04-01 至 2014-03-31
• 项目状态: 已结题
• 来源: https://kaken.nii.ac.jp/en/grant/KAKENHI-PROJECT-24658105/
• 关键词: nigricanoside; amphidinolide; cytotoxic; antimitotic; glycolipid; macrolide; topsentolide; oxylipin; 細胞毒性

Toward the determination of the stereochemistry of nigricanoside A, a marine-derived glycolipid bearing an unprecedented structural pattern and a potent antimitotic activity, the synthesis of its highly oxygenated alpha- and beta-fatty acid chains has been accomplished. Its southeastern segment consisting of a galactosyl glycerol unit and the right-hand portion of the bata-chain has also been synthesized. The segment is planned to connect with a northwestern segment of the target molecule by the Julia-Kocienski coupling reaction. Synthetic study on the 26-membered macrolide amphidinolide N has also been undertaken and the preparation of its C7-C13 portion has been completed by using an asymmetric vinylogous Mukaiyama aldol reaction (Kobayashi aldol reaction) as the key step.

为了确定黑果苷A的立体化学，具有前所未有的结构模式和有效的抗有丝分裂活性的海洋来源的糖脂，其高度氧化的α-和β-脂肪酸链的合成已经完成。它的东南部分由一个半乳糖基甘油单元和右手部分的β链也已合成。该片段计划通过Julia-Kocienski偶联反应与目标分子的西北部分连接。对26元大环内酯环丙二烯N的合成进行了研究，并以不对称乙烯基向山羟醛缩合反应（小林羟醛缩合反应）为关键步骤，完成了环丙二烯N的C7-C13部分的合成。

项目成果

Synthesis of topsentolides A_2 and C_2, and non-enzymatic conversion of the former to the latter

托普生内酯A_2和C_2的合成，以及前者向后者的非酶转化

• DOI: 10.1016/j.tet.2014.04.040
• 发表时间: 2014
• 期刊: Tetrahedron
• 影响因子: 2.1
• 作者: Ryo Towada;Shigefumi Kuwahara
• 通讯作者: Shigefumi Kuwahara

topsentolide C2およびA2の合成研究

托普生内酯C2和A2的合成研究

• 发表时间: 2014
• 作者: 猪又直子;ら;十和田諒，倉科友輔，桑原重文
• 通讯作者: 十和田諒，倉科友輔，桑原重文

生物有機化学分野ホームページ

生物有机化学领域主页

Stereoselective Synthesis of a Protected Form of (6<I>R</I>,7<I>E</I>,9<I>S</I>,10<I>R</I>,12<I>Z</I>)-6,9,10-Trihydroxy-7,12-hexadecadienoic Acid

(6<I>R</I>,7<I>E</I>,9<I>S</I>,10<I>R</I>,12< 保护形式的立体选择性合成

• DOI: 10.1271/bbb.110829
• 发表时间: 2012
• 期刊: Bioscience, Biotechnology, and Biochemistry
• 作者: Yusuke Kurashina;Shigefumi Kuwahara
• 通讯作者: Shigefumi Kuwahara

Nigricanoside類の絶対立体配置決定にむけた合成研究

确定黑果苷绝对构型的合成研究

• 发表时间: 2013
• 作者: Inomata N;Okazaki F;Moriyama T;Nomura Y;Narita H;Aihara M;倉科友輔,十和田諒,桑原重文
• 通讯作者: 倉科友輔,十和田諒,桑原重文