1143-54-0

Usage

InChI:InChI=1/C15H23NO/c1-11-3-5-14-12(2)4-6-15(16(14)9-11)13-7-8-17-10-13/h7-8,10-12,14-15H,3-6,9H2,1-2H3/t11-,12+,14-,15-/m0/s1

Upstream product

• 60161-30-0 4-(furan-3-yl)-1-methyl-7-methyleneoctahydro-2H-quinolizine 
• 113689-18-2 (1R,4S,9aS)-4-(3-furyl)-1,7-dimethyl-1,3,4,5,9,9a-hexahydro-2H-quinolizine 
• 468-89-3 nupharidine 
• 62724-10-1 1,7-dimethyl-4-(3-furyl)quinolizidin-2-one 
• 62740-41-4 3-(5-methyl-2-pyridyl)butan-2-one ethylene acetal 
• 62740-46-9 3-(5-methyl-2-pyridyl)butan-2-one 
• 18113-81-0 2-ethyl-5-methylpyridine 
• 96791-40-1 (R)-1,7-Dimethyl-1,2,3,8,9,9a-hexahydro-quinolizin-4-one 
• 616866-58-1 (R)-4-[(S)-5-methylene-1-(toluene-4-sulfonyl)piperidin-2-yl]pent-2-enoic acid ethyl ester 
• 616866-56-9 N-{1-[2-(tert-butyldimethylsilanyloxy)-1-methylethyl]-4-(hydroxymethyl)pent-4-enyl}-4-methylbenzenesulfonamide 
• 616866-52-5 2(S)-[2-(tert-butyl-dimethyl-silanyloxy)-1(S)-methyl-ethyl]-5-methylene-1-(toluene-4-sulfonyl)-piperidine 
• 616866-50-3 2(S)-[2-(tert-butyl-dimethyl-silanyloxy)-1(S)-methyl-ethyl]-N-(p-toluenesulfonyl)-aziridine 
• 616866-65-0 (S)-2-[(S)-5-methylene-1-(toluene-4-sulfonyl)piperidin-2-yl]propan-1-ol 
• 616866-46-7 (2R,3S)-N-(p-toluenesulfonyl)-3-methylaspartic acid dimethyl ester 

Relevant academic research and scientific papers

Stereoselective synthesis of Nuphar quinolizidine alkaloid, (-)-deoxynupharidine

A stereoselective synthetic route to Nuphar quinolizidine alkaloid, (-)-deoxynupharidine, was established by employing reductive carbon-nitrogen bond cleavage, followed by simultaneous recyclization of a proline derivative with samarium diiodide, and an intramolecular ring-closing metathesis, as the key steps.

Novel chiral synthetic path to indolizidine and quinolizidine alkaloids by means of a samarium diiodide-promoted reductive carbon-nitrogen cleavage reaction: Synthesis of (+)-(8R, 8aR)-perhydro-8-indolizidinol and (-)-deoxynupharidine

Novel chiral synthetic procedures for indolizidine and quinolizidine alkaloids were developed, where a samarium diiodide-promoted carbon-nitrogen bond cleavage reaction was employed as a key step. Application of the procedure led to the total synthesis of (+)-(8R, 8aR)-perhydro-8-indolizidinol and (-)-deoxynupharidine.

Development of a flexible approach to Nuphar alkaloids via two enantiospecific piperidine-forming reactions

(Chemical Equation Presented). In this paper we describe the stereoselective synthesis of functionalized lactam 7 via two enantiospecific piperidine-forming techniques and its employment in a general synthetic approach to Nuphar alkaloids. Specifically, the formation of piperidine 18 by formal [3 + 3] cycloaddition and stepwise annelation processes is described; the latter technique was found to be significantly more efficient than the Pd-catalyzed TMM addition process. Finally, exploitation of the exocyclic alkene installed in the piperidine-forming reaction in the transformation of 18 to (-)-deoxynupharidine ((-)-2), (-)-castoramine ((-)-3), and (-)-nupharolutine ((-)-4) via intermediate lactam 7 is delineated.

Diels-Alder Reaction of 1-Azadienes. A Total Synthesis of Deoxynupharidine

The Diels-Alder reaction of a N-acyl-1-azadiene was a key step in the total synthesis of the quinolizidine alkaloid (-)-deoxynupharidine.