2000 Fiscal Year Final Research Report Summary
New development of synthesis of aromatic heterocycles using A novel palladium-phosphine ligand reagent
| Project/Area Number |
11672103
|
|---|
| Research Category |
Grant-in-Aid for Scientific Research (C)
|
| Allocation Type | Single-year Grants |
|---|
| Section | 一般 |
|---|
| Research Field |
Chemical pharmacy
|
|---|
| Research Institution | OKAYAMA UNIVERSITY |
|---|
Principal Investigator |
HARAYAMA Takashi Faculty of Pharmaceutical Sciences, OKAYAMA UNIVERSITY, Professor, 薬学部, 教授 (30025712)
|
|---|
| Project Period (FY) |
1999 – 2000
|
| Keywords | Palladium reagent / benzo [c] phenanthridine / chelerythrine / Aryl-aryl coupling / 12-methoxydihydrochelerythrine / norchelerythrine / trisphaeridine / benzo [d] naphthopyran |
|---|
| Research Abstract |
1) Investigation of general synthetic method for chelerythrine type alkaloid
A novel palladium reagent prepared from equimolar palladium acetate, DPPP, and tributylphophine was useful for the inernal biaryl coupling reaction of benzanilide possessing not only triflate but also halogen as a leaving group. By using this novel Pd reagent, benzo [c] phenanthridine alkaloids, chelerythrine, 12-methoxydihydrochelerythrine, and norchelerythrine were synthesized in good yields.. Benzo [d] naphtopyranones, arnottin I, was also synthesized by using typical Heck's reaction conditions.
2) Mechanistic aspect of novel Palladium reagent [palladium acetate, DPPP, and tributylphophine]
It was found out that molar ratio of Pd : phosphine=1 : 3 is essentially necessary for biaryl coupling reaction
3) Synthesis of phenolic benzo [c] phenanthridine alkaloid
Fagaridine was synthesized in a good yield via biaryl coupling reaction of benzanilide protected by isopropyl group followed by reduction and acid treatment.
4) Synthetic studies on Amaryllidaceae alkaloid, trisphaeridine
Phenanthridine alkaloid, trisphaeridine, was synthesized via biaryl coupling reaction using palladium reagent.
|
