1990 Fiscal Year Final Research Report Summary
Synthetic Studies on Biologically Active Substances for Retaining Homeostasis
| Project/Area Number |
01470141
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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 | Teikyo University |
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Principal Investigator |
IKEGAMI Shiro Teikyo Univ., Fac. Pharm. Sci., Prof., 薬学部, 教授 (10119555)
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| Co-Investigator(Kenkyū-buntansha) |
YANAGIYA Yuki Teikyo Univ., Fac. Pharm. Sci. Res. Assoc., 薬学部, 助手 (10200544)
WATANABE Nobuhide Teikyo Univ., Fac. Pharm. Sci., Res. Assoc., 薬学部, 助手 (80220911)
MIYAZAKI Yoji Teikyo Univ., Fac. Pharm. Sci., Res. Assoc., 薬学部, 助手 (70211597)
HONDA Takeshi Teikyo Univ., Fac. Pharm. Sci., Res. Assoc., 薬学部, 助手 (60173663)
HASHIMOTO Shun-ichi Teikyo Univ., Fac. Pharm. Sci., Assoc. Prof., 薬学部, 助教授 (80107391)
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| Project Period (FY) |
1989 – 1990
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| Keywords | Prostacyclin / Isocarbacyclin / Rhodium(II) carboxylates / Carbenoid / Organolead reagents / Glycosylation / Glycosides / beta-Keto esters |
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| Research Abstract |
A result of our research carried out in 1989-1990 is summarized as follows.
1) A new synthetic route to isocarbacyclin which is a potential analogue of prostacyclin discovered in our laboratory was established by employing a C-H insertion reaction of rhodium-carbenoid for the synthesis of a synthetic intermediate and the direct introduction of a omega chain with a 1-alkenyllead reagent for the construction of a secondary synthetic intermediate.
2) An improvement of rhodium (II) catalyst for a C-H insertion reaction was studied and a variety of homochiral rhodium carboxylates were prepared for the construction of chiral molecules.
3) An efficient and selective synthesis of alpha- (EPSILON and ZETA) -1-alkenyl ketones was established by the combination of a regio- and stereocontrolled introduction of (EPSILON) -1-alkenyl and the corresponding ZETA groups to beta-Keto esters and subsequent reductive removal of ester functionali
ty.
4) A higly stereoselective glycosidation by modifying leaving groups involving a phosphorus atom as the best glycosyl donor was extensively studied. The glycosidation method we established was applied to synthesize some anti-tumor agent and further applications are continuously investigated.
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