1995 Fiscal Year Final Research Report Summary
Preparation and Utilization of Chiral Synthons of Cyclopentadienone and Cyclohexadienone
| Project/Area Number |
06672083
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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 |
Chemical pharmacy
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| Research Institution | TOHOKU UNIVERSITY |
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Principal Investigator |
OGASAWARA Kunio Toboku Univereity, Pharmaceutical Institute, Professor, 薬学部, 教授 (60004602)
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| Project Period (FY) |
1994 – 1995
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| Keywords | chiral building block / chiral cyclopentadienone synthon / chiral cyclohexadienone synthon / enantiocontrolled synthesis / enzymatic reaction / chiral ligand-metal complex catalyst / lipase-mediated reaction / meso-asymmetrization |
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| Research Abstract |
Chiral equivalents of cyclopentadienone and cyclohexadienone have been prepared by employing lipase-mediated asymmetric transesterification and hydrolysis and by employing chiral ligand-metal complex catalyst.
Basis of the present investigation is the convex-face selective reaction on the enone system of tricyclic synthons having bicyclo [2.2.1] heptane framework and their cleavage by retro Diels-Alder reaction to regenerate the double bond originated from cyclopentadienone and cyclohexadienone precursors.
The high functionality and versatile utilities of the chiral synthons of cyclopentadienone and cyclohexadienone prepared have been demonstrated by the syntheses of a wide variety of biologically active natural products such as alpha-aminoacids, terpenes, steroids, alkaloids, and polyketides.
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