| Project/Area Number |
62570953
|
|---|
| Research Category |
Grant-in-Aid for General Scientific Research (C)
|
| Allocation Type | Single-year Grants |
|---|
| Research Field |
Chemical pharmacy
|
|---|
| Research Institution | Tokyo College of Pharmacy |
|---|
Principal Investigator |
KIBAYASHI Chihiro Tokyo College of Pharmacy, 薬学部, 教授 (80057330)
|
|---|
| Project Period (FY) |
1987 – 1988
|
| Project Status |
Completed (Fiscal Year 1988)
|
| Budget Amount *help |
¥1,900,000 (Direct Cost: ¥1,900,000)
Fiscal Year 1988: ¥300,000 (Direct Cost: ¥300,000)
Fiscal Year 1987: ¥1,600,000 (Direct Cost: ¥1,600,000)
|
|---|
| Keywords | Asymmetric 1,3-Dipolar Cycloaddition / Nitrone / (S)-Allyl Ether / Inside Alkoxy Transition State / (-)-Coniine / (+) -モノモリン I / 不斉1,3ー双極子環付加反応 / (+)-モノモリン I |
|---|
| Research Abstract |
Asymmetric 1,3-dipolar cycloaddition of nitrones by using a chiral allyl ether as a dipolarophile and application to an enantioselective synthesis of (-)-coniine and (+)-monomorine I has been investigated. The cyclic and acyclic nitrones were allowed to react with (s)-3-benzyloxy-1-heptene, resulting in the preferential formation (3:1) of the (2R,3aS)-and (3S,5R)-isoxazolidine derivatives, respectively, predicted by application of the inside alkoxy more reactive conformation in a transition state. These cycloadducts were enantiomerically converted to (-)-coniine and (+)-monomorine I,respectively.
|
