Synthesis of anti-viral Carbocyclic Nucleosides by Stereosclective Control of Cycloaddition Reactions.
| Project/Area Number | 06651012 |
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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 |
Synthetic chemistry
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| Research Institution | Kagoshima University |
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Principal Investigator |
SOMEKAWA Kenichi Kagoshima Univ., Fac.of Eng., Professor, 工学部, 教授 (10041534)
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| Co-Investigator(Kenkyū-buntansha) |
UEMURA Hisako Kagoshima Univ., Fac.of Eng., Research Assoc., 工学部, 助手 (20041535)
SHIMO Tetsuro Kagoshima Univ., Fac.of Eng., Associate Prof, 工学部, 助教授 (80041565)
村岡 富美子 鹿児島大学, 工学部, 教務職員 (90229948)
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| Project Period (FY) |
1994 – 1995
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| Project Status |
Completed(Fiscal Year 1995)
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| Budget Amount *help |
¥1,300,000 (Direct Cost : ¥1,300,000)
Fiscal Year 1995 : ¥500,000 (Direct Cost : ¥500,000)
Fiscal Year 1994 : ¥800,000 (Direct Cost : ¥800,000)
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| Keywords | HIV / Anti-virnus / Photocycloaddition / C-nucleosides / Carbocyclic-Oxetanocins / 炭素環ヌクレオシド / 抗ウイルス |
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| Research Abstract |
Some carbocyclic oxetanocins exibit wide antiviral and potent anti-HIV activities. Several synthetic methods for the oxetanocins have been reported. Such studies are quite important as a scientific challenge against AIDS.
We have describe improved and facile methods to synthesize a chiral exetanocin and the analogues by way of much shortened routes employing photocycloadditions of maleic anhydrides with vinyl acetate as the key-step reactions.
An endo-[2+2]cycloadduct prepared by the photoreaction was derived to some chiral cyclobutan-dicarboxylates and coupled with adenine to give carbocyclic oxetanocins, but the mothods was not effective for the optical ones. An adenine-cyclobutane-dicarboxylate was optically resolved using a chiral acid and is being subjected for reduction to give a chiral carbocyclic oxetanocin.
The oxetanocin analogues were derived via photoreactions of methylmaleic anhydride with vinyl acetate. The reactions are also effective for mechanistic analysis of the coupling and reduction reactions.
On the other hand, many photocycloaddition reactions between two different type of molecules were investigated in non-solution systems and the factors for steric selectivity on the [2+2]cycloadditions were analyzed, and it was inferred that some ground state interactions between the two molecules influenced to the steric selectivity.
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Report
(3results)
Research Products
(12results)
