1988 Fiscal Year Final Research Report Summary
Synthesis of Biologically Active Compounds from Chiral Natural Products
| Project/Area Number |
62870087
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| Research Category |
Grant-in-Aid for Developmental Scientific Research
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| Allocation Type | Single-year Grants |
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| Research Field |
Chemical pharmacy
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| Research Institution | Kyushu University |
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Principal Investigator |
SAKAI Kiyoshi Kyushu University, 薬学部, 教授 (90153840)
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| Co-Investigator(Kenkyū-buntansha) |
FUNAKOSHI Kazuhisa Kyushu University, 薬学部, 助手 (50037579)
SUEMUNE Hiroshi Kyushu University, 薬学部, 助手 (20095897)
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| Project Period (FY) |
1987 – 1988
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| Keywords | Limonene / Prostaglandin / Rhodium (I) complex / Carbacyclin / 立体選択的閉環反応 |
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| Research Abstract |
The results of this project were as follows:
1) Chemical conversion of (+)-limonene to prostaglandin (PG) E_2 could be almost established on the basis of stereoselective RH(I)-catalysed cyclization.
2) Carbacyclin was synthesized from (+)-limonen-10-ol by using RH(I)-catalysed cyclization, regioselective aldol condensation, and diastereoselective 1,4-addidion.
3) PGE_1 was synthesized by the new route on the basis of air-oxidation of cyclopentenones, chiral induction by microbial reduction, and diastereo- and chemo-selective conversion.
4) New ring conversion under acetalization condition, which was found in this project, was clarified to be effective for conversion from five membered ring to five ro six membered ring.
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