| Project/Area Number |
13672243
|
|---|
| Research Category |
Grant-in-Aid for Scientific Research (C)
|
| Allocation Type | Single-year Grants |
|---|
| Section | 一般 |
|---|
| Research Field |
Chemical pharmacy
|
|---|
| Research Institution | Kyoto Pharmaceutical University |
|---|
Principal Investigator |
IKEDA Masazumi Kyoto Pharmaceutical University, Faculty of Pharmaceutical Sciences, Professor, 薬学部, 教授 (30028857)
|
|---|
| Co-Investigator(Kenkyū-buntansha) |
YAKURA Takayuki Kyoto Pharmaceutical University, Faculty of Pharmaceutical Sciences, Assistant Professor, 薬学部, 講師 (70220126)
|
|---|
| Project Period (FY) |
2001 – 2002
|
| Project Status |
Completed (Fiscal Year 2002)
|
| Budget Amount *help |
¥3,500,000 (Direct Cost: ¥3,500,000)
Fiscal Year 2002: ¥1,500,000 (Direct Cost: ¥1,500,000)
Fiscal Year 2001: ¥2,000,000 (Direct Cost: ¥2,000,000)
|
|---|
| Keywords | dirhodium(II) catalyst / C-H insertion reaction / chemo- and stereo-selective / α-diazoketone / cyclpentanone / 3(2H)-furanone / β-hydroxy acid / cyclization / αーアルコシキジアゾケトン / ロジウム(II)触媒C-H挿入反応 / 2-ジヒドロフラノン / 不斉合成 / 無溶媒Baeyer-Villiger反応 / 抗腫瘍活性海洋天然物 / dicodermolide / prelactoneC |
|---|
| Research Abstract |
Development of novel highly chemo- and stereo-selective dirhodium(II)-catalyzed C-H insertion reaction of α-diazoketones controlled by stereo-electronic effect of tert-butyldimethosilyl group was achieved. As a result, a variety of functionalized cyclpentanones have been easily prepared. And the new acceleration method of the Baeyer-Villiger reaction of polysubstituted cyclopentanones was found to give polysubstituted δ-lactones. These new reactions applied to efficient syntheses of Corey lactone, an important intermediate of prostagrandins, and lactone portion of antitumor marine antibiotics discodermolide.
A new methodology for the asymmetric synthesis of β-hydroxy acid was developed. Dirhodium(II)-catalyzed C-H insertion of α-alkoxydiazoketone, which was prepared from primary alkyl halide and readily available chiral α-hydroxy acid, gave stereoselectively 2,5-cis-disubstituted 3(2H)-furanone. The furanone was converted to chiral β-hydroxy acid with high optical purity.
|
