1987 Fiscal Year Final Research Report Summary
Synthesis of Antibiotics having Benzonaphthopyran Ring System using Lithiation Reaction
| Project/Area Number |
61571008
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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 | Nagasaki University |
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Principal Investigator |
WATANABE Mitsuaki Nagasaki University, Faculty of Pharmaceutical Sciences, 薬学部, 助手 (10039654)
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| Project Period (FY) |
1986 – 1987
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| Keywords | lithiation reaction / ortho-toluamide / toluamide anion / homophthalic acid anhydride / benzonaphthopyran / WS-5995A |
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| Research Abstract |
The directed lithiation reaction of tertiary benzamide derivatives has been developed into a significant method for the regiospecific construction of polysubstituted aromatics. In this research, the usefullness of the directed lithiation strategy was demonstrated in the synthesis of WS-5995 A methylether.
WS-5995 A was isolated from streptomyces auranticolor in 1980, and it protected chickens from infection with Eimeria tenella. Its structure was elucidated as 5H-benzo[d]naphtho[2,3-b]pyran derivatives. For the synthesis of WS-5995 A and the related compounds, ortho-toluamides and homophthalic acid anhydrideswere selected as the starting materials. WS-5995 A methylether was synthesized in 5 steps via 2-aryl-1,3-naphthol derivatives which were obtained by the formal insersion reaction of ortho-toluamide anions into homophthalic acid anhydrides as the key reaction.
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