Asymmetric Synthesis Using Acetals : Formation of Chiral Oxonium Ion
| Project/Area Number |
14572005
|
|---|
| Research Category |
Grant-in-Aid for Scientific Research (C)
|
| Allocation Type | Single-year Grants |
|---|
| Section | 一般 |
|---|
| Research Field |
Chemical pharmacy
|
|---|
| Research Institution | Osaka University |
|---|
Principal Investigator |
FUJIOKA Hiromichi Osaka University, Graduate School of Pharmaceutical Sciences, Associate Professor, 薬学研究科, 助教授 (10173410)
|
|---|
| Project Period (FY) |
2002 – 2003
|
| Project Status |
Completed (Fiscal Year 2003)
|
| Budget Amount *help |
¥3,500,000 (Direct Cost: ¥3,500,000)
Fiscal Year 2003: ¥1,700,000 (Direct Cost: ¥1,700,000)
Fiscal Year 2002: ¥1,800,000 (Direct Cost: ¥1,800,000)
|
|---|
| Keywords | (R, R)-hydrobenzoin / asymmetric desymmetrization / stenine / scyphostatin / acyclic σ-symmetic diene acetal / domino haloetherification / optically active tetrahydrofuran / シクロヘキサジエンアセタール / 3-エンドフェニルノルボルネンアルデヒド / メソ-ジオール |
|---|
| Research Abstract |
Formations of chiral oxonium ion intermediates by intramolecular haloetherification of ene acetals and their applications have been investigated.
As an application of the chiral, non-racemic cyclohexene acetal obtained by an intramolecular haloetherification reaction of cyclohexadiene acetal from 3-(1,4-cyclohaxadien-3-yl)propanal and chiral hydrohenzoin, synthetic work of stemona alkaloids was held. As a result, 9a-epi-stenine has been achieved, and the synthesis of stenine itself is on the last stage. From the intermediate of their syntheses, the epoxy cyclohexenone core of scyphostatin having N-Smase inhibiting activity was synthesized.
Furthermore, an unexpected domino intramolecular haloetherification reaction of acyclic σ-symmetic diene acetals was found, and the tetrahyderofurans having four asymmetric centers were obtained in one-pot operation.
|
Report
(3 results)
Research Products
(15 results)
-
-
-
-
-
[Journal Article] Concise Asymmetric Synthesis of a Model Compound, (4S,5S,6S)-6-(2,2-Dimethoxy) Ethyl-4,5-epoxy-6-hydroxy-2-cyclohexenone, for the Cyclohexenone Core of Scyphostatin2002
Author(s)
H.Fujioka, N.Kotoku, Y.Sawama, Y.Nagatomi, Y.Kita
-
Journal Title
Tetrahedron Lett. 43
Pages: 4825-4828
Description
「研究成果報告書概要(欧文)」より
Related Report
-
-
-
-
-
-
-
-
-
-
