1990 Fiscal Year Final Research Report Summary
Preparation of An Optically Active Building Block Having A Quaternary Carbon Center and Synthesis of Euonyminol
| Project/Area Number |
01540443
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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 |
有機化学一般
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| Research Institution | Okayama University of Science |
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Principal Investigator |
UENISHI Junichi Okayama Univ. of Sci. Faculty of Science, Lecture, 理学部, 講師 (50167285)
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| Co-Investigator(Kenkyū-buntansha) |
WAKABAYASHI Shoji Okayama Univ. of Sci. Faculty of Science, Professor, 理学部, 教授 (40068870)
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| Project Period (FY) |
1989 – 1990
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| Keywords | quaternary carbon / building block / PIFA / lipase / cyclization / euonyminol / acetomycin |
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| Research Abstract |
1. Preparation of optically active building blocks having a quaternary carbon center
(1) A various kinds of small building blockshaving a quaternary carbon center were synthesized from diethyl malonate by several steps.
(2) The utility of these building blocks was demonstrated by accomplishment of the total synthesis of anticancer antibiotics acetomycin.
(3) Although some attempts in preparation of optically active building blocks have benn failed, a kinetic resolution by lipase hydrolysis of some acetate derivatives having tetrahydrofuran ring, e. g. shown in the right, was successfully to give optical active alcohol. The highest degree of enantio excess become up to be 55-60 %.
2. Synthetic approaches to euonyminol
(1) A new aldol type of reaction between 1, 3-dithiane and ethyl vinyl ether mediated by PIFA (phenyliodosyl bistrifluoroacetate) was found, which was used for construction of the A ring of euonyminol.
(2) A key bond forming reaction in construction of the B ring was achieved by using SmI_2 mediated pinacol coupling reaction in the model substrates.
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