86 分子内アミノ環化反応を用いる効率的なアルカロイドのキラル合成(ポスター発表の部)
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There have been found, in the venom of ants and poisons from frogs, a variety of the pyrrolidine, piperidine, pyrrolizidine, and indolizidine system bearing alkyl appendages. However, the absolute configuration of most of these compounds remains unknown because of their short supply from natural sources. During the course of our program directed towards the design and development of new strategies for the asymmetric synthesis of biologically active nitrogen-containing compounds, we disclose a short and stereoselective synthesis of the abovementioned alkaloids employing an intramolecular amidomercuration of N-alkenylurethanes available from α-amino acids. The intramolecular amidomercuration of N-benzyloxycarbonyl-4-pentenylamines using mercuric acetate (kinetic control condition) gave preferentially trans-α,α'-disubstituted pyrroildines. On the other hand, N-benzyloxycarbonyl-5-hexenylamines underwent the intramolecular amidomercuration with mercuric trifluoroacetate (thermodynamic control condition) to afford cis-α,α'-disubstituted piperidines preferentially. The functionalized pyrrolidines and piperidines have been chirospecifically transformed into several alkaloids such as trans-2,5-dialkylpyrrolidines (ant venom and poison from flog), 3,5-dialkylpyrrolizidines (ant venom), pinidine, 3,5-dialkylindolizidine alkaloids (ant venoms and poisons from flog).
- 天然有機化合物討論会の論文
- 1992-09-10
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