1995 Fiscal Year Final Research Report Summary
Precise Synthesis of Unnatural Nucleosides
| Project/Area Number |
06453061
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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 |
物質変換
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| Research Institution | Chiba University |
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Principal Investigator |
YOKOYAM Masataka Chiba University Department of Chemistry, Faculty of Science, 理学部, 教授 (00009052)
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| Project Period (FY) |
1994 – 1995
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| Keywords | C-Nucleosides / C-Ribonucleosides / Ribosyl fluoride / Ribosyl radical / Stereoselectivity / C-Deoxyribonucleosides / Mitsunobu reaction / C-Heteroatom-nucleosides |
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| Research Abstract |
Nucleic acid is a fundamental element for the construction of living body. Its behabior is not clear completely even if its function is generally understandable. Our purpose is the establishment of its general and useful synthetic method accessible for chemists. Especially our target compound is a C-nucleoside, whose typical one is showdomycin.
In the course of 1994 to 1995, we have established a general synthetic methodology for C-nucleosides even though a precise synthesis is not completed yet. Our methodology consists of (1)A stereoselective reaction of protected ribose with lithium salts of base compounds and (2)A stereospecific cyclization of the dithiol derivatives thus obtained uner the Mitsunobu conditions.
On the other hand, the ribosyl fluoride, a stable sugar donor, reacts with base moiety especially such as indole derivatives in high yields stereoselectively. Furthermore, the synthetic method which utilizes the ribosyl radical as the sugar donor, has advantage in the coupling of sugar moiety with the bases which are difficult for electrophilic substitution. Now the synthesis of C-heteroatom-nucleosides which has heteroatom such as metal as sugar moiety is in progress.
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