Development of New Methodologies for the efficient synthesis of biologically active compounds

开发有效合成生物活性化合物的新方法

基本信息

批准号：
12660101
负责人：
TANIMORI Shinji
金额：
$ 0.45万
依托单位：
Osaka Prefecture Unicersity
依托单位国家：
日本
项目类别：
Grant-in-Aid for Scientific Research (C)
财政年份：
2000
资助国家：
日本
起止时间：
2000 至 2001
项目状态：
已结题

项目摘要

1. Development of transition metal-catalyzed tandem organi reactionReaction of 2-butenylene dicarbonate with primary amine was catalyzed by palladium-phosphine catalyst to produce novel 5-vinyl oxazolidone in good yield. Asymmetric induction of this reaction was achieved by using chiral bidentate phosphine ligand to produce chiral oxazolidone derivatives in 90 % enantio selectivity.2. Synthetic approach for both enantiomars of jasmonic acidReaction of meso-1, 4-diacetoxycyclopentene with dimethyl malonate in the presence of palladium-chiral phosphine catalyst possessing C_2-symmetry to give alkylated product in 85 % enentiomeric purity. The product was converted into knouw intermedate for the synthesis of jasmonic acid.3. Synthetic approach for asperparaline, an indolidine alkaloid posessing potent Paralytic activityEnyne derived from praline was subjected to Pauson-Khand cycloaddition using cobalt octacarbonyl to produce tricyclic indolidine, which was treated with methylamine to gibe teracyclic bridged amide, a potential intermediated for asperparaline C in good yield.4 Synthetic approach for cyclic ADP-ribose, a second messenger for Ca^<2+> releaseEfficient chemical synthesis of NMN and derivatives, a precursor of NAD, was developed Reaction of tetraacetate prepared fron D-ribose with nicotinamide in the presence of Lewis acid (TMSOTf) followed by treatment of methanol to provide NAR, which was phopholylated to give desired NMN in good yield.

1。通过钯 - 磷酸催化剂催化2-丁烯基二烯烃与原代胺的过渡金属催化的串联有机体反应，以良好产量产生新型的5-乙烯基沙唑酮。通过使用手性双齿磷酸配体在90％对映体选择性中产生手性黄唑酮衍生物。2。在钯 - 毒性磷脂催化剂存在下，具有C_2对称性的MESO-1，4-二氧基环戊酸的茉莉酸反应的合成方法，具有85％的eNentiomericericersic purity。将产物转化为中间盐中的中介物以合成茉莉酸3。芦丁碱的合成方法，一种吲哚胺的生物碱作用，从praline得出的有效的麻痹活性烯烃被使用使用钴核酸的pauson-khand Cycloadition进行，以产生三环吲哚胺，以甲基胺的甲基甲基甲基甲基的甲基甲基甲基甲基甲烷的良好为中心，以产生三环吲哚胺，以此类环环ADP-核糖的方法是，NMN和衍生物的Ca^<2+>释放效率化学合成的第二个使者是NAD的前体，是NAD的前体，在链醇酸（TMSOTF）的情况下与烟醇相关的甲醇处理中的四乙酸酯D-ribose与烟酰胺的反应，可提供nar酚，从而提供了narlyl nar的nar酚。