Synthetic Study of Pradimicns, Antiviral Antibiotics Possessing the Binding Abilities to Oligosacchrides
| Project/Area Number |
10440214
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| Research Category |
Grant-in-Aid for Scientific Research (B)
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| Allocation Type | Single-year Grants |
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| Section | 一般 |
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| Research Field |
物質変換
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| Research Institution | Tokyo Institute of Technology |
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Principal Investigator |
SUZUKI Keisuke Graduate School of Science and Engineering, TOKYO INSTITUTE OF TECHNOLOGY, Prof., 大学院・理工学研究科, 教授 (90162940)
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| Co-Investigator(Kenkyū-buntansha) |
OHMORI Ken Graduate School of Science and Engineering, TOKYO INSTITUTE OF TECHNOLOGY, Research Associate, 大学院・理工学研究科, 助手 (50282819)
MATSUMOTO Takashi Graduate School of Science and Engineering, TOKYO INSTITUTE OF TECHNOLOGY, Associate Prof., 大学院・理工学研究科, 助教授 (70212222)
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| Project Period (FY) |
1998 – 1999
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| Project Status |
Completed (Fiscal Year 1999)
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| Budget Amount *help |
¥13,400,000 (Direct Cost: ¥13,400,000)
Fiscal Year 1999: ¥1,400,000 (Direct Cost: ¥1,400,000)
Fiscal Year 1998: ¥12,000,000 (Direct Cost: ¥12,000,000)
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| Keywords | Pradimicin / Benanomicin / Antibiotics / Total Synthesis / ヨウ化サマリウム / ピナコール生成反応 |
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| Research Abstract |
The pradimicin-benanomicin antibiotics constitute a new class of natural products with a benzo[a]naphthacenequinone core wkh an amino acid and a disaccharide.They show anti-fungal and anti-HIV activities, which are related to the selective binding abilities to mannose-rich oligosaccharides, e.g. the mannane surface of fungi or gp 120 of HIV. The unique structure as well as the significant biological activities led me to undertake the synthesis of this class of compounds.
The most intriguing challenge among the synthetic issues is the control of the vicinal diol stereogenicities at the corner of the pentacyclic skeleton comprises, to which we explored the possible use of intramolecular pinacol coupling of bis-aldehyde. Along these lines, we found that this reaction is useful for the above issue.
The SmIィイD22ィエD2-mediated pinacol coupling of biphenyl o, o'-dialdehyde was found to proceed stereo selectivelly and gave only trans diol, which enabled us to achieve the synthesis of the trans diol structure of B ring as diastereomerically pure form. Furthermore, the reaction proved to proceed stereospecifically, thereby enabling the full transmission of the axial chirality into the two central chiralities. Thus, we studied the stereoselective and -specific pinacol coupling of bis-aldehyde, providing the requisite trans-diol in enantio- and diastereomerically pure form, which served as a basic strategy for the total synthesis of the pradimicin-benanomicin class antibiotics.
Total synthesis of the pradimicinone (benanomicinone), the common aglycon of the class of natural products, based on the above mentioned pinacol cyclization, has been achieved.
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Report
(3 results)
Research Products
(8 results)
