1998 Fiscal Year Final Research Report Summary
Synthetic studies of hybrid macrolides.
| Project/Area Number |
08557124
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| Research Category |
Grant-in-Aid for Scientific Research (A)
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| Allocation Type | Single-year Grants |
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| Section | 展開研究 |
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| Research Field |
Chemical pharmacy
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| Research Institution | Okayama University of Science |
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Principal Investigator |
YONEMITSU Osamu Okayama University of Science, Faculty of Science Professor, 理学部, 教授 (60001038)
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| Co-Investigator(Kenkyū-buntansha) |
NAKAJIMA Noriyuki Toyama Prefectural University, Biotechnology Research Center Associate Professor, 工学部・生物高額研究センター, 助教授 (40188959)
UENISHI Jun-ich Okayama University of Science, Faculty of Science Professor, 理学部, 教授 (50167285)
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| Project Period (FY) |
1996 – 1998
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| Keywords | macrolide / stereoselective synthesis / cyclization / glucose / protecting group / hybrid / keto-phosphonate |
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| Research Abstract |
The purpose of this research was to develop a new synthetic methodology of a series of complex natural and artificial macrolides through convenient and efficient syntheses of many fragments and their couplings starting from inexpensive materials such as glucose. The following three results were mainly obtained during the past three years research.
1.Synthetic studies of natural macrolides : Recently, we developed two methods for the constructioi on of macro-rings ; macrolactonization and Horner-Emmons cycization of the corresponding seco acids and aldehyde-ketophosphonates, respectively. This methodology, combined with computer aided conformational analysis (using both molecular mechanics and molecular orbital calculations) and structural design of key intermediates, was successfully applied to a highly efficient synthesis of the 18-membered lactone of tedanolide, an antitumor marine macrolide. The improved synthesis of key fragments of tedanolide was also completed.
2.Synthetic studies of artificial macrolide : The enone and dienon type typical macrolides such as methynolide, pikronolide, tylonolide, carbonolides were aynthesized via coupling of the corresponding two fragments followed by Horner-Emmons cyclization. In order to obtain artificial macrolides, exchange of fragment combinations were tried, but only a few successful results were so far available.
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