1993 Fiscal Year Final Research Report Summary
Development of Synthetic Methods toward Biologically Active Compou
| Project/Area Number |
04640491
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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 |
有機化学一般
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| Research Institution | Chiba University |
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Principal Investigator |
YOKOYAMA Masataka Professor of Chemistry Faculty of Science Chiba University, 理学部, 教授 (00009052)
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| Co-Investigator(Kenkyū-buntansha) |
TOGO Hideo Assistant Department of Chemistry Faculty of Science Chiba University, 理学部, 助手 (60217461)
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| Project Period (FY) |
1992 – 1993
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| Keywords | C-Nucleosides / D-Ribosyl Radical / D-Deoxyribosyl Radical / Trivalent Iodine Compounds / Barton Reaction / Photochemical Reaction / Thermal Reaction / Tetrakis (TMS) silanes |
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| Research Abstract |
In order to synthesize many kinds of C-nucleosides, we intended to combine D-ribosyl and D-deoxyribosyl radicals with N-containing aromatic heterocycles. As the radical reagents, diphenylselenium diacyloxylate, (diacyloxyiodo)benzene, tetrakis(trimethylsilyl)silane, and thiohydroxamic acid ester known as the Barton reagent were examined under photochemical and thermal conditions.
The result showed that the Barton reaction could be applicable for the C-nucleoside synthesis. Therefore several C-nucleosides were synthesized by employing the Barton reaction. The other reagents required the further investigation for the C-nucleoside synthesis.
Next, the synthesis of C-nucleosides was performed by utilizing the ionic reaction : the lithium salt of typical aromatic heterocycles was introduced onto the benzyl-protected D-ribose followed by the acid-cyclization.
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