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- W2153521832 abstract "A mild oxidative deamination reaction of tetrahydroanabasine O-methyloxime 17 is described, making use of an o-quinone that is based on topaquinone (TPQ, 11), the cofactor that is present in copper-containing amine oxidases. In situ ring closure of the oxidation product produced double-functionalized quinolizidine 5, containing an enamine functionality with excellent reactivity. From this quinolizidine 5 a variety of biogenetically related lupin alkaloids were prepared: lupinine (7) and aminolupinane (8) via reductive sequences and sparteine (9) via a condensation reaction with dehydropiperidine 1. The configurationally more favorable trans isomers epilupinine (25) and β-isosparteine (10) were formed when more drastic reaction conditions were used for oxime hydrolysis. Anabasine (4) and a new 5-piperidylanabasine derivative 6 were formed by an unexpected acid catalyzed ring transformation reaction, whereby the pyridine ring was formed via oxime-induced aromatization. The stereochemistry of the reaction products and the biogenetic implications are discussed." @default.
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- W2153521832 title "Oxidative Deamination of Tetrahydroanabasine with <i>o</i>-Quinones: An Easy Entry to Lupinine, Sparteine, and Anabasine" @default.
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- W2153521832 doi "https://doi.org/10.1021/jo9602130" @default.
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