| Project/Area Number |
62470133
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| Research Category |
Grant-in-Aid for General Scientific Research (B)
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| Allocation Type | Single-year Grants |
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| Research Field |
Chemical pharmacy
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| Research Institution | Hokkaido University |
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Principal Investigator |
SHIBASAKI Masakatsu Faculty of Pharmaceutical Sciences, Professor, 薬学部, 教授 (30112767)
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| Co-Investigator(Kenkyū-buntansha) |
SODEOKA Mikiko Faculty of Pharmaceutical Sciences, Instructor, 薬学部, 助手 (60192142)
MORI Miwako Faculty of Pharmaceutical Sciences, Assistant Professor, 薬学部, 助教授 (80001981)
森 美和子 北海道大学, 薬学部, 助教授 (78001981)
吉田 清史 北海道大学, 薬学部, 助手 (60109478)
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| Project Period (FY) |
1987 – 1989
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| Project Status |
Completed (Fiscal Year 1990)
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| Budget Amount *help |
¥7,700,000 (Direct Cost: ¥7,700,000)
Fiscal Year 1989: ¥800,000 (Direct Cost: ¥800,000)
Fiscal Year 1988: ¥1,900,000 (Direct Cost: ¥1,900,000)
Fiscal Year 1987: ¥5,000,000 (Direct Cost: ¥5,000,000)
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| Keywords | Silyl Dienol Ether / Prostacyclin Derivative / Beta-Lactam / Cr(CO)_3 Complex / Copper Triflate / Isomerization Reaction / β-ラクタム / クロムカルボニル錯体 / コッパ-トリフレ-ト / 抗潰瘍剤 / エノールエーテル / シリルジエノールエーテル / クロムトリカルボニル錯体 / カルバペネム抗生物質 / ペネム抗生物質 / プロスはサイクリン誘導体 |
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| Research Abstract |
We have succeeded in development of the new stereoselective reactions and their application to the synthesis of biologically important compounds as follows.
1. The stereocontrolled synthesis of aryl-substituted exocyclic olefins has been achieved for the first time by utilizing naphthalene・Cr (CO)_3 catalyzed isomerization of conjugated dienes as a key step.
2. The stereocontrolled synthesis of silyl dienol ethers having E, Z-configurations has been achieved for the first time by utilizing naphthalene・Cr (CO)_3 catalyzed isomerization of conjugated dienes.
3. A highly efficient synthesis of antiulcer nileprost has been achieved by utilizing reduction-isomerization reaction of the conjugated dienes.
4. Cu (I) OTf has been found to be an extremely useful reagent for the synthesis of beta-lactams from beta-amino thiol esters.
5. The eastern part of azadirachtin has been synthesized starting with malic acid.
6. A catalytic asymmetric synthesis of cis-decalin derivatives has been achieved by utilizing Heck-type reaction of prochiral alkenyl iodides.
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