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

Autor:	Christian V. Stevens, Norbert De Kimpe
Rok vydání:	1993
Předmět:	chemistry.chemical_classification Aldimine Stereochemistry Organic Chemistry Acetaldehyde Stenus comma Alkylation Aldehyde chemistry.chemical_compound Hydrolysis chemistry Yield (chemistry) Organic chemistry Piperidine
Zdroj:	The Journal of Organic Chemistry. 58:132-134
ISSN:	1520-6904 0022-3263
DOI:	10.1021/jo00053a025
Popis:	Stenusine [1-ethyl-3-(2-methylbutyl)piperidine], the spreading agent of Stenus comma, was synthesized by a six-step sequence in 21 % 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 delta-chloro aldimine was hydrolyzed into the delta-chloro aldehyde, which was converted into the corresponding N-ethyl aldimine. The latter labile delta-chloro aldimine was cyclized with lithium aluminum hydride to afford stenusine. The 1-tert-butyl analogue of stenusine was synthesized using an analogous route.
Databáze:	OpenAIRE
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