486-72-6

Upstream product

• 53439-74-0 1-carbethoxy-4-quinolizidinone 
• 408330-49-4 1-methyleneoctahydro-1H-quinolizine 
• 120001-35-6 ((4-bromopent-4-en-1-yl)oxy)(tert-butyl)dimethylsilane 
• 694-54-2 tetrahydro-2H-2-pyranol 

Relevant academic research and scientific papers

Piperidine and azetidine formation by direct cyclization of diols with N-nonsubstituted sulfonamide under the Mitsunobu conditions utilizing (cyanomethylene)tributylphosphorane (CMBP) and its application to the synthesis of lupinine

(Cyanomethylene)tributylphosphorane (CMBP) can promote the Mitsunobu reaction of 1,3- and 1,5-diols with N-nonsubstituted sulfonamides, such as tosylamide (TsNH2) and 3,3-dimethoxypropylsulfonamide (DimpsNH2), to prepare azetidine and piperidine ring systems directly. Utilizing this methodology, lupinine, a biologically active piperidine alkaloid, was synthesized.

Oxidative deamination of tetrahydroanabasine with o-quinones: An easy entry to lupinine, sparteine, and anabasine

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.

SYNTHESIS OF (+/-)-LUPININE AND (+/-)-EPI-LUPININE USING REGIOSELECTIVE ALKYLATION OF FUNCTIONALIZED 3-SULFOLENE

The regioselective alkylation of 3-(N,N-dimethylaminomethyl)-3-sulfolene was applied to the synthesis of quinolizidine alkaloids, (+/-)-lupinine and (+/-)-epi-lupinine.