| Project/Area Number |
03670987
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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 | HOKKAIDO UNIVERSITY |
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Principal Investigator |
HAMADA Tatsuo Hokkaido University,Faculty of Pharmaceutical Sciences,Associate Professor, 薬学部, 助教授 (40001979)
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| Co-Investigator(Kenkyū-buntansha) |
NAKAJIMA Noriyuki Hokkaido University,Faculty of Pharmaceutical Sciences,Lecturer, 薬学部, 助手 (40188959)
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| Project Period (FY) |
1991 – 1992
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| Project Status |
Completed (Fiscal Year 1992)
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| Budget Amount *help |
¥2,100,000 (Direct Cost: ¥2,100,000)
Fiscal Year 1992: ¥500,000 (Direct Cost: ¥500,000)
Fiscal Year 1991: ¥1,600,000 (Direct Cost: ¥1,600,000)
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| Keywords | macrolide antibiotics / total synthesis / seco-acid / conformation / calculation / macrolactonization / Retro synthetic analysis / マクロリド抗生物貭 |
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| Research Abstract |
To complete the total synthesis of macrolide antibiotics like 5 and 6, macrolactonization of seco-acid derivatives 3 into macrolactone is generally the most critical step. To design the most reasonable seco-acid to synthesize macrolactone, we calculated conformations of seco-acids (1 and 2), then actually synthesized 1 and 2. Those seco-acids were subjected to macrolactonization and the results of the conformation calculation and the ease of lactonization were compared. Seco-acid 1a has chair conformation of 6-membered acetal of C9 and C11 diol and at several persent population there exist the conformer having confor-mation close to lactone 3a and the lactonization is predicted to be so easy.
The total synthesis of oleandonolide 5 was completed by lactonization of 1a to give 3a and conversion of 3a to 5.
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