1987 Fiscal Year Final Research Report Summary
Studies on the Development of Practical Electroorganic %reactions Associated with Biological Processes
| Project/Area Number |
60470089
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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 |
有機工業化学
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| Research Institution | Okayama University |
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Principal Investigator |
TORII Sigeru Okayama University, School of Engineering, Professor, 工学部, 教授 (70032927)
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| Co-Investigator(Kenkyū-buntansha) |
INOKUCHI Tsutomu Okayama University, School of Engineering, Instructor, 工学部, 教務員 (50168473)
OKUMOTO Hiroshi Okayama University, School of Engineering, Instructor, 工学部, 助手 (90183251)
TANAKA Hideo Okayama University, School of Engineering, Assistant Professor, 工学部, 助教授 (60032950)
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| Project Period (FY) |
1985 – 1987
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| Keywords | Chiralbuilding block / Electroorganic reaction / Chiral synthon / Penicillin / Cephalosporin Selenation / Ruthenium tetraoxide / Halogen / 電解セレン化 / 四酸化ルテニウム / グルコース / 光学活性菊酸 / 電解エン型塩素化法 / 間接電解酸化 / ルテニウム化合物 |
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| Research Abstract |
Use of chiral building blocks easily accessible from natural bio-mass is of current topics in the synthesis of bio-active compounds. This research project concerns with (A) electrochemical transformations of chiral bio-mass into versatile chiral synthons and their synthetic applications and (B) conversion of biochemically produced penicillin derivatives into the valuable cephalosporin compounds by electrochemical means and their applications. In the research project (A), we developed an efficient functional group preparing methods based on electoorganic reactions, i.e. selenation-deselenation sequence, (2) selective ring rearrangement of oxiranes, (3) ruthenium tetraoxide mediated oxidation of alcohols, (4) halogen mediated ring cleavage of furans, and others. Synthetic utilities of these methodologies are shown in the synthesis of useful bio-active compounds such as karahanaenone from dehydrolynalilyl acetate and chrysanthemic acids from (+)-3-carene, and others. In second research program (B), we have succeeded in the selective ene-type chlorination of prenyl moiety of azetidinones. The procedure has been extended in the practial synthesis of a variety of cepharosporin analogues. Conversion of 3'-chlorocephalosporins into the corresponding 3-methylenecephams is also investigated.
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