The Journal of Organic Chemistry

Synthesis of stenusine, the spreading agent of the beetle Stenus comma

C Stevens, N De Kimpe

文献索引：Stevens, Christian; Kimpe, Norbert de Journal of Organic Chemistry, 1993 , vol. 58, # 1 p. 132 - 134

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被引用次数: 34

摘要

Stenusine [l-ethyl-3-(2-methylbutyl) piperidinel, the spreading agent of Stenus comma, was synthesized by a six-step sequence in 21 7% overall yield from acetaldehyde. Acetaldehyde was converted into the corresponding N-tert-butyl aldimine, which was sequentially alkylated via its 1-azaallylic anion with 1-bromo-2-methylbutane and 1-bromo-3- chloropropane. The resulting 6-chloro aldimine was hydrolyzed into the 3-chloro aldehyde ...