1998 Fiscal Year Final Research Report Summary
Transition Metals-Mediated Efficient Synthesis of Biologically Active Natural Products.
| Project/Area Number |
09672164
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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 | Tokyo University of Pharmacy and Life Science |
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Principal Investigator |
OHTA Akihiro Tokyo University of Pharmacy and Life Science, School of Pharmacy, Professor, 薬学部, 教授 (90057307)
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| Co-Investigator(Kenkyū-buntansha) |
INABA Haruko Tokyo University of Pharmacy and Life Science, School of Pharmacy, Research Fell, 薬学部, 助手 (40277257)
UCHIYAMA Masahiko Tokyo University of Pharmacy and Life Science, School of Pharmacy, Research Fell, 薬学部, 助手 (40277265)
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| Project Period (FY) |
1997 – 1998
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| Keywords | Palladium Catalyst / Pyrrole / Indole / beta-Hydroxy-enamine / Garner Aldehyde / (2R,3S)-2-Hydroxymethyl-3-hydroxypyrrolidine / (+)-Bulgecine |
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| Research Abstract |
1. Palladium-Catalyzed Efficient Synthesis of Pyrroles and Indoles
Palladium-catalyzed oxidation of beta-hydroxy-enamine, which was easily prepared from amino alcohols and beta-keroesters, and subsequent cyclization gave the corresponding polysubstituted pyrroles in good yields. On the other hand, treatment of 2'-hydroxyethylaniline derivatives with palladium catalyst and mesityl bromide gave the corresponding 2-and 3-substituted indoles. 4-Oxo-5,6,7,8-tetrahydroindoles, which might be starting materials of ergot alkaloids, were also prepared under the same reaction conditions. The procedure developed in this project have several merits as shown below ; 1) catalytic amount of palladium salts is necessary, 2) catalysts could be recycled, 3) good yields, 4) starting materials are prepared easily or purchased, and 5) basic or almost neutral medium.
2. Chromium Chloride-Mediated Asymmetric Carbon-Carbon Bond Formation Reaction and its Synthetic Application to Biologically Active Natural Products
The Chromium(II) chloride-mediated coupling reactions of Garner aldehydes with allyl bromides gave the corresponding homoallyl alcohols in good yields with moderate to good stereoselectivity. Thus obtained homoallyl alcohols were converted to several biologically active natural products such as (2R,3S)-2-hydroxymethyl-3-hydroxypyrrolidine, (2R, 3R, 4R)-3-hydroxy-4-methylproline, and (+)-bulgecinine in short steps. We are also examining to synthesize sulfobacin now.
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