| Project/Area Number |
61570991
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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 |
SUGAHARA Tsutomu Tohoku University, Research Assistant, 薬学部, 助手 (50006350)
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| Project Period (FY) |
1986 – 1987
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| Project Status |
Completed (Fiscal Year 1987)
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| Budget Amount *help |
¥1,800,000 (Direct Cost: ¥1,800,000)
Fiscal Year 1987: ¥300,000 (Direct Cost: ¥300,000)
Fiscal Year 1986: ¥1,500,000 (Direct Cost: ¥1,500,000)
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| Keywords | Halenaquinone / (-)-Wieland-Miescher ketone / Intramolecular [2+2]photocyclization / 3環性フラン / (R)-(-)-Wieland-Miescherケトン / アセチレン化合物 / 2+2光環化反応 / 3環式フラン |
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| Research Abstract |
According to the synthetic strategy for Halenaquinone (1), Halenaquinol (2) and Xestoquinone (3), (-)-Wieland-Miescher ketone (4) was transformed to acetylenic , -unsaturated ketone (5) by 14 steps. Tricyclic cyclobutene ketone (6) was prepared by intramolecular [2+2]photocycloaddition of (5). Ozonolysis of (6) followed by treatment with acid and ethylene glycol afforded the chiral key synthetic intermediate (7). Unfortunately hydrogenolysis of (7) led to a complex mixture of products from which desired alcohol (8) could be isolated in only ca. 25% yield. Next p-methoxybenzyl group was employed for the protection of hydroxyl group. According to the above mentioned general synthetic route, acetylenic <alpha>, <beta>-unsaturated ketone (9) was converted to tricyclic furan ring compound (10) by same procedures. Conversion of (10) into halenaguinone (1) is now under investigation.
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