2007 Fiscal Year Final Research Report Summary
SYNTHETIC STUDIES OF NATURAL PRODUCTS DIRECTED TOWARD MEDICINAL SOURCES BY ELECTROCYCLIC REACTIONS
| Project/Area Number |
17590025
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| Research Category |
Grant-in-Aid for Scientific Research (C)
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| Allocation Type | Single-year Grants |
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| Section | 一般 |
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| Research Field |
Chemical pharmacy
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| Research Institution | Fukuyama University |
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Principal Investigator |
HIBINO Satoshi Fukuyama University, FACULTY OF PHARMACY AND PHARMACEUTICAL SOCIETY, PROFESSOR (60112885)
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| Co-Investigator(Kenkyū-buntansha) |
CHOSHI Tominari Fukuyama University, FACULTY OF PHARMACY AND PHARMACEUTICAL SCIETY, ASOCIATE PROFESSOR (10248297)
NOBUHIRO Junko Fukuyama University, FACULTY OF PHARMACY AND PHARMACEUTICAL SCIENCE, 助手 (70352002)
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| Project Period (FY) |
2005 – 2007
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| Keywords | ELECTROCYCLIC REACTION / LAVANDUQUINOCIN / CARBAZOMADURIN A AND B / β-CARBOLINE / DICHOTOMINE A-D / NEUROKININ RECEPTOR ANTAGONIST / CP-728663 |
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| Research Abstract |
(1) Synthetic study of lavanduquinocin: An asymmetric synthesis of the core carbazole structure, 6-desprenyl-carquinostatin and 6-descycloavandulyl-lavanduquinocin, toward a total synthesis of carquinostatin and lavanduquinocin, has been established by the lipase QLM catalyzed enantioselective acetylation of the racemic alcohol. The absolute stereochemistry of the (-)-and (+)-alcohol have been determined to be R- and S-configurations, respectively, by the advanced Mosher method. Finally, oxidation of (R)-(-)-alcohol and (S)-(+)-alcohol gave R-(-)-6-descycloavandulyl-lavanduquinocin and its enantiomer, respectively.
(2) Synthetic study of carbazomadurin : An appropriate 1, 2, 3, 5, 7-pentasubstututed carbazole has been synthesized by an allene-mediated electrocyclic reaction involving the indole 2, 3-bond. We are now a final stage for the total synthesis of carbazomadurin A.
(3) Synthetic study of dichotomine A-D and dichotomide I and II: A total synthesis of dichotomine C has been completed by an electrocyclic reaction of aza 6π-electron system, followed by asymmetric oxidation. Further studies are now in progress.
.(4) Synthetic study of CP-728663 having neurokinine receptor antagonist: The 2-quinolone part has been synthesized by an electrocyclic reaction of 2-aza 6p-electron system involving the benzene 2, 3-bond. On the other hand, a part of 4-amino-2-ethyl-6-phenylpiperidine are now investigation on the final stage.
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