| Project/Area Number |
63570992
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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 | Osaka University |
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Principal Investigator |
IMANISHI Takeshi Osaka Univ., Fac. of Pharm. Sci., Professor, 薬学部, 教授 (40028866)
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| Project Period (FY) |
1988 – 1989
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| Project Status |
Completed (Fiscal Year 1989)
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| Budget Amount *help |
¥2,000,000 (Direct Cost: ¥2,000,000)
Fiscal Year 1989: ¥600,000 (Direct Cost: ¥600,000)
Fiscal Year 1988: ¥1,400,000 (Direct Cost: ¥1,400,000)
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| Keywords | Natural product synthesis / Bond cleavage of cyclopronae ring / Sesquiterpene / Polyquinane / Pentalenene / Quadrone / 抗腫瘍活性 / クァドロン類縁体 / シクロプロパン / 全合成 / 立体選択性 / 制癌作用 |
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| Research Abstract |
Polyquinane framework plays an important role of structural unit of many kinds of naturally occurring organic compounds, some of which exhibit significantly biological activities. In this project, a couple of poluquinane sesquiterpenes were successfully synthesized by the use of a common intermediate 1 which was subjected to regioselective C-C bond cleavage of cyclopropane ring.
The Birch reduction of 1 exclusively afforded the bicyclo 3.3.0 octane 2 via C_2-C_8 bond fission of the cyclopropane ring, while treatment of 1 under nucleophilic substitution conditions gave the bicyclo 3.2.1 octane 3 as a main product via the C_1-C_2 ond cleavage. On the other hand, the carboxylic acid 4, easily obtained from 1, afforded the lactone 5 efficiently through the exclusive C_1-C_2 bond fission by an intramolecular carboxylic acid participation.
Through the several-step sequence starting from 2, total synthesis of a representative triqyinane sesquiterpene pentalenene (6) was accomplished.
Descarboxyquadrone (7) and an antitumor diquinane sesquiterpene quardrone (9) were also synthesized by the use of key intermediates 3 and 8,respectively.
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