1990 Fiscal Year Final Research Report Summary
Development of New Stereoselective Reaction and its Application
| Project/Area Number |
62470133
|
|---|
| Research Category |
Grant-in-Aid for General Scientific Research (B)
|
| Allocation Type | Single-year Grants |
|---|
| Research Field |
Chemical pharmacy
|
|---|
| Research Institution | Hokkaido University |
|---|
Principal Investigator |
SHIBASAKI Masakatsu Faculty of Pharmaceutical Sciences, Professor, 薬学部, 教授 (30112767)
|
|---|
| Co-Investigator(Kenkyū-buntansha) |
SODEOKA Mikiko Faculty of Pharmaceutical Sciences, Instructor, 薬学部, 助手 (60192142)
MORI Miwako Faculty of Pharmaceutical Sciences, Assistant Professor, 薬学部, 助教授 (80001981)
|
|---|
| Project Period (FY) |
1987 – 1989
|
| Keywords | Silyl Dienol Ether / Prostacyclin Derivative / Beta-Lactam / Cr(CO)_3 Complex / Copper Triflate / Isomerization Reaction |
|---|
| Research Abstract |
We have succeeded in development of the new stereoselective reactions and their application to the synthesis of biologically important compounds as follows.
1. The stereocontrolled synthesis of aryl-substituted exocyclic olefins has been achieved for the first time by utilizing naphthalene・Cr (CO)_3 catalyzed isomerization of conjugated dienes as a key step.
2. The stereocontrolled synthesis of silyl dienol ethers having E, Z-configurations has been achieved for the first time by utilizing naphthalene・Cr (CO)_3 catalyzed isomerization of conjugated dienes.
3. A highly efficient synthesis of antiulcer nileprost has been achieved by utilizing reduction-isomerization reaction of the conjugated dienes.
4. Cu (I) OTf has been found to be an extremely useful reagent for the synthesis of beta-lactams from beta-amino thiol esters.
5. The eastern part of azadirachtin has been synthesized starting with malic acid.
6. A catalytic asymmetric synthesis of cis-decalin derivatives has been achieved by utilizing Heck-type reaction of prochiral alkenyl iodides.
|
