权益分类	功能权益	普通用户	{{item.name}}会员
{{category.name}}	{{benefitItem.name}}

Exploitation of Chiral Epichlorohydrin as Versatile Chiral Building Block

手性环氧氯丙烷作为多功能手性构件的开发

基本信息

批准号：
07557288
负责人：
OGASAWARA Kunio
金额：
$ 4.16万
依托单位：
TOHOKU UNIVERSITY
依托单位国家：
日本
项目类别：
Grant-in-Aid for Scientific Research (A)
财政年份：
1995
资助国家：
日本
起止时间：
1995 至 1997
项目状态：
已结题

来源：
https://kaken.nii.ac.jp/grant/KAKENHI-PROJECT-07557288/
关键词：
epichlorohydrin chiral building block enantiocontrolled synthesis muscarine O-benzylglycidol fish deterrent vitamin D HMG-CoA reductase コレステロール生合成阻害剤 HMG Co-A還元酵素阻害 compactin mevinolin カルシウム代謝ホルモン calcitriol 活性型ビタミンD 生体抗酸化物質

项目摘要

Epichlorohydrin was obtained practically in enantiomerically pure forms by fermentation in our country. In order to exploit enantiomerically pure epichlorohydrin as versatile chiral building block, we have investigated enantiocontrolled construction of a variety of physiologically active natural products including amino acids, alkaloids, polyketides, terpenes, and steroids. During a 1995-1997 period, we have been engaged in the enantiocontrolled syntheses of "Sporochnol A", the fish deterrent from the Caribbean Marine alge, "carbazoquinocins A and D", the potent lipid peroxidation inhibitors from Streptomyces violaceus 2248-SVT2, "compactin lactone", the essential structural component associated with the biological activity of the potent HMG-CoA reductase compactin, "calcitriol enyne", the a ring component of the activated form of vitamin D,"dihydroxyheliotridane", a physiologically interesting necine base, and "muscarine and three naturally occurring its diastereomers", mushroom poisons exhibiting potent anticholinergic activity. Among these compounds obtained, the absolute configurations of sporochnol A,carbazoquinocins A and D were determined by these syntheses by correlation to the absolute configuration of epichlorohydrin used as the starting material.

在我国，环氧氯丙烷实际上是以对映体纯的形式通过发酵获得的。为了利用对映体纯的环氧氯丙烷作为通用的手性结构单元，我们研究了对映体控制的各种生理活性天然产物的构建，包括氨基酸，生物碱，聚酮化合物，萜烯和甾体。在1995-1997年期间，我们从事了对映体控制合成“Sporochnol A”，来自加勒比海海藻的鱼类威慑物，“卡巴喹诺辛A和D”，来自紫色链霉菌2248-SVT 2的有效脂质过氧化抑制剂，“compactin内酯”，与有效HMG-CoA还原酶compactin的生物活性相关的基本结构组分，“骨化三醇烯炔”，维生素D的活化形式的α环组分，“二羟基天芥菜碱”，一种生理上令人感兴趣的necine碱，和“毒蝇碱和三种天然存在的其非对映异构体”，表现出有效的抗胆碱能活性的蘑菇毒素。在这些化合物中，sporochnol A，carbazoquinocins A和D的绝对构型是通过这些合成通过与用作起始原料的环氧氯丙烷的绝对构型的相关性来确定的。