Efficient enantiomeric synthesis of pyrrolidine and piperidine alkaloids from tobacco

…, G Vo-Thanh, RJ Robins, J Villiéras…

文献索引：Felpin; Girard; Vo-Thanh; Robins; Villieras; Lebreton Journal of Organic Chemistry, 2001 , vol. 66, # 19 p. 6305 - 6312

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被引用次数: 135

摘要

An enantiomeric synthesis of six piperidine and pyrrolidine alkaloids,(S)-nornicotine 1,(S)- nicotine 2,(S)-anatabine 3,(S)-N-methylanatabine 4,(S)-anabasine 5, and (S)-N- methylanabasine 6, known as natural products in tobacco, was established from a common chiral homoallylic (S)-3-(1-azido-but-3-enyl)-pyridine 15. An intramolecular hydroboration- cycloalkylation of the homoallylic azide intermediate 15 served as the key step in the ...