1993 Fiscal Year Final Research Report Summary
Synthesis of Marine Synomone "Aplysinopsin" Related Compounds
| Project/Area Number |
04671305
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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 | Kitasato University, School of pharmaceutical Sciences |
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Principal Investigator |
ZEN Shonosuke Kitasato Univ., School of Pharmaceutical Sciences, Professor, 薬学部, 教授 (80050342)
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| Co-Investigator(Kenkyū-buntansha) |
HIROTANI Seiko Kitasato Univ., School of Pharmaceutical Sciences, Assistant Researcher, 薬学部, 助手 (20050594)
HIROOKA Motoko Kitasato Univ., School of Pharmaceutical Sciences, Assistant Researcher, 薬学部, 助手 (20050578)
HARADA Kazuho Kitasato Univ., School of Pharmaceutical sciences, Assistant Researcher, 薬学部, 助手 (00189698)
KAJI Eisuke Kitasato Univ., School of Pharmaceutical Sciences, Research Associate, 薬学部, 講師 (60050598)
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| Project Period (FY) |
1992 – 1993
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| Keywords | Marine synomone / Aplysinopsin / Isoxazoine-2-oxide / Benzofuroisoxazole / Ring transformation / Titanium tetrachloride / Indole-1-oxide |
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| Research Abstract |
In order to synthesize the related compound of antitumor marine synomon "Aplysinopin", the reactins of 3,5-bis(methoxycarbonyl)-2-isoxazoline-2-oxide derivatioves with titanium tetrachloride were investigated as follows :
1. The reaction of 4-(m-substituted phenyl)-3,5-bis(methoxycarbonyl)-2-isoxazoline-2-oxides with titanium tetrachloride did not afford desired 3H-indole-1-oxides, but alpha-hydroxy-4H-1,2-benzoxazines were isolated.
The latter compunds were converted to 2-oxo-2H-benzofuro[2,3-b]pyrroles in a thre step sequence.
2.4-(p-Substituted phenyl)-3,5-bis(methoxycarbonyl)-2-isoxazoline-2-oxides were reacted with titanium tetrachlride to afford benzofuro[3,3a-d]-isoxazoles and their Diels-Alder dimers.
3.5-Hydroxymethyl-3-methoxycarbonyl-4-(p-substituted phenyl)-2-isoxazoline-2-oxides converted to benzofuro[2,3-c]tetrahydrofurans and benzofuro-[3,2-d]-1,2-oxazines by the action of titanium tetrachloride.
4. The reaction of 4-indolyl-3,5-bis(methoxycarbonyl)-2-isoxazoline-2-oxide with titanium tetrachloride yielded desired alpha-hydroxyindo[2,3-b]-1-pyrrole-1-oxiede, which can be the synthetic precursor of the related comound of antitumor marine synomone "Aplysinopusin".
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