| Project/Area Number |
01571139
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| Research Category |
Grant-in-Aid for General Scientific Research (C)
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| Allocation Type | Single-year Grants |
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| Research Field |
Chemical pharmacy
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| Research Institution | Department of Pharmaceutical Science, Akita University |
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Principal Investigator |
SUZUKI Toshio Akita University of Medicine, Pharmaceutical Science, Associate Professor, 医学部, 助教授 (20108559)
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| Co-Investigator(Kenkyū-buntansha) |
UNO Katsuo Akita University of Medicine, Pharmaceutical Science, Professor, 医学部, 教授 (40111322)
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| Project Period (FY) |
1989 – 1991
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| Project Status |
Completed (Fiscal Year 1991)
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| Budget Amount *help |
¥2,200,000 (Direct Cost: ¥2,200,000)
Fiscal Year 1991: ¥700,000 (Direct Cost: ¥700,000)
Fiscal Year 1990: ¥700,000 (Direct Cost: ¥700,000)
Fiscal Year 1989: ¥800,000 (Direct Cost: ¥800,000)
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| Keywords | D-Mannitol / L-Ascorbic acid / Claisen rearrangement / Cyclopentanone derivative / Steroid / (-)-Chokol A / Vitamin D_3 / Brefeldin A / アスコンビン酸 / 光学活性シクロペンタノン誘導体 / (ー)ーchokol A / ヒルスタン型セスキテルペン / tricyclo〔6.3.0.0AA2.6BB〕undecane / 〔3.3.0〕octane誘導体 / (R)ーグリセルアルデヒド / (S)ーグリセルアルデヒド / クライゼン転位反応 / サイクロペンタノン誘導体 / トランスーヒドリンダン骨格 / ステロイド類 / ビタミンD類 / D-マンニト-ル / アスコルビン酸 / (R)-グリセルアルデヒド / (S)-グリセルアルデヒド / Claisen転位 / キラリティ / cyclepextanone誘導体 / α-mettylene-r-butyrolactone |
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| Research Abstract |
Enantioselective syntheses of various types of natural products were examined based on a biosynthetic pathway. Namely, four chiral cyclopentanone derivatives (1), (2), (3) and (4) were synthesized via 1, 2-0-isopropylideneglyceraldehyde from D-mannitol and L-ascorbic acid using Claisen rearrangement as a key step.
<<chemical formula>>
Trans-hydrindanone propion acid (5) bicyclo[3.3.0]octane (6) and (-)-chokol A (7) were synthesized from the compound (2). whereas de-AB-cholestane derivative (8). key intermediate for construction of vitamin D3. was obtained from the compound (4). During the course of the syntheses of steroids. fortunately. we are able to develop steroids possessing extremely strong anti-inflamatory activity and non pituitary adrenal suppression. so called -antedrug- and "pro-antedrug-". Furthermore. trans-hydrindanone (9) and cyclopentanone derivative (10) were synthesized by intramolecular ring opening of the corresponding epoxides. respectively. These cyclized products could also be important intermediates for construction of 1, 25(OH)_2 vitamin D_3 and brefeldin A possessing antifungal, antiviral and other biological activities.
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