| Project/Area Number |
13650904
|
|---|
| Research Category |
Grant-in-Aid for Scientific Research (C)
|
| Allocation Type | Single-year Grants |
|---|
| Section | 一般 |
|---|
| Research Field |
有機工業化学
|
|---|
| Research Institution | Osaka University |
|---|
Principal Investigator |
NOJIMA Masatomo Osaka University Graduate School of Engineering, Professor, 大学院・工学研究科, 教授 (80029181)
|
|---|
| Project Period (FY) |
2001 – 2002
|
| Project Status |
Completed (Fiscal Year 2002)
|
| Budget Amount *help |
¥1,200,000 (Direct Cost: ¥1,200,000)
Fiscal Year 2002: ¥1,200,000 (Direct Cost: ¥1,200,000)
|
|---|
| Keywords | Macrocyclic Peroxides / Unsaturated Hvdroperoxides / BCIH-promoted Cyclization / Ozonation / Antimalarial Agents / BCHI プロモータ環化 / 大環状過酸化物 / 求電子的分子内環化反応 / ヨウ素イオン / SCIHメディエータ / 酸素酸化 |
|---|
| Research Abstract |
Since malaria parasites are rapidly developing resistance to the most commonly used chemo-tnerapeutic alkaloidal drugs, the antimalarial properties of nonalkaloidal compounds such as artemisinin have attracted considerable attention. Based on our original methodologies for the synthesis of medium-sized cyclic peroxides, we tried to develop new synthetic methods of macrocyclic peroxides. The key starting material is unsaturated hydroperoxides, which could be prepared by the mono-alkylation of 1, 1 -bishydroperoxides or selective oxidation of one of the double bonds of dienes. Bis(syn-collidine)iodine(l) hexafluorophosphate-promoted cyclization of the derived unsaturated hydroperoxides was found to give the corresponding 11- to 20-membered cyclic peroxides in excellent yields. Alternatively, ozonolyses of unsaturated hydroperoxides in trifluoroethanol gave the hydroperoxysubstituted cyclic peroxides including the 13-membred one, derived from intramolecular capture of the carbonyl oxide moiety by the hydroperoxy group. We are now investigating the biological activities of these macrocyclic peroxides.
|
