1988 Fiscal Year Final Research Report Summary
Studies on the Total Synthesis of Tetronolide
| Project/Area Number |
62570933
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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 | Toyama Medical and Pharmaceutical University |
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Principal Investigator |
YOSHII Eiichi Toyama Medical and Pharmaceutical University (Professor), 薬学部, 教授 (50019105)
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| Co-Investigator(Kenkyū-buntansha) |
HORI Kozo Toyama Medical and Pharmaceutical University (Assistant), 薬学部, 教務員 (50173612)
TAKEDA Kei Toyama Medical and Pharmaceutical University (Assistant), 薬学部, 助手 (30135032)
NOMURA Keiichi Toyama Medical and Pharmaceutical University (Professor), 薬学部, 教授 (30019111)
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| Project Period (FY) |
1987 – 1988
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| Keywords | Total Synthesis / Tetronolide / Kijanolide / Tetronic Acid / Spiroannulation / ディールス-アルダー反応 |
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| Research Abstract |
Tetronolide, the aglycone of the antitumor antibiotic tetrocarcins, is structurally unique 13-membered ketone containing a spirotetronic acid and a hydronaphthalene nucleus as the bridging units. Our strategy in the tetronolide syntheses consitutes three major aspects: stereoselective synthesis of the two subunits and joining them to form the macrocyclic ketone structure. In this study, we have achievded the synthesis of the tetronic acid containing upper fragment and the lower octaline portion, both in optically active forms. We have also developed an efficent technique for the construction of the macrocyclic structure as applied to the synthesis of bisnorkijanolide. Furthermore, we have established an easy access to the spirotetronic acid fragment of chlorothricolide (the aglycone of a macrolide antibiotic chlorothricin which is a close analogue of tetronolide).
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