1993 Fiscal Year Final Research Report Summary
Preparation and Utilization of Chiral Building Blocks Having Bicyclo[2.2.1]heptane Ring System
| Project/Area Number |
03453152
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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 |
Chemical pharmacy
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| Research Institution | TOHOKU UNIVERSITY |
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Principal Investigator |
TAKANO Seiichi Tohoku University, Pharmaceutical Institute, Professor, 薬学部, 教授 (20004559)
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| Co-Investigator(Kenkyū-buntansha) |
SUGAHARA Tsutomu Tohoku University, Pharmaceutical Institute, Research Associate, 薬学部, 助手 (50006350)
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| Project Period (FY) |
1991 – 1993
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| Keywords | Chiral building block / Chiral cyclopentadienone synthon / Chiral cyclohexadienone synthon / Chiral bicyclo[2.2.1]heptane system / Lipase-mediated resolution / Enantiomerization / Asymmetrization of mesomer / Retro-Diels-Alder Cleavage |
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| Research Abstract |
Two chiral building blocks having bicyclo[2.2.1]heptane ring system have been prepared by employing lipase mediated resolution as the key step. Namely, optically pure ketodicyclopentadiene serving as chiral equivalent of cyclopentadienone was prepared from dicyclopentadiene by empoying either lipase mediated asymmetric esterification or deacylation reaction. An efficient procedure for the enantiomerization has also been established. On the other hand, optically pure homoketodicyclopentadiene serving as chiral equivalent of cyclohexadienone was prepared in both enatiomeric forms from the Diels-Alder adduct of p-benzoquinone and cyclopentadiene by asymmetrization via the lipase-mediated enantiospecific mono-esterification of the meso-symmetric intermediate.
Based on molecular bias of these componds owing to the bicyclo[2.2.1]heptane ring system and facile retro-Diels-Alder removal of cyclopentadiene, a variety of physiologically active natural products ranging from a simple monoterpene to a complex polyoxygenated plant toxin have been synthesized in a complete stereocontrolled way.
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