616866-50-3

Upstream product

• 18162-48-6 tert-butyldimethylsilyl chloride 
• 616866-42-3 2(S)-[N-(p-toluenesulfonyl)-aziridin-2(S)-yl]-propan-1-ol 
• 616866-48-9 (1R,2S)-N-(3-hydroxy-1-hydroxymethyl-2-methyl-propyl)-4-methylbenzenesulfonamide 

Downstream Products

• 616866-52-5 2(S)-[2-(tert-butyl-dimethyl-silanyloxy)-1(S)-methyl-ethyl]-5-methylene-1-(toluene-4-sulfonyl)-piperidine 
• 616866-56-9 N-{1-[2-(tert-butyldimethylsilanyloxy)-1-methylethyl]-4-(hydroxymethyl)pent-4-enyl}-4-methylbenzenesulfonamide 
• 38681-18-4 nupharolutine 
• 6874-86-8 (–)-castoramine 
• 1143-54-0 deoxynupharidine 
• 616866-65-0 (S)-2-[(S)-5-methylene-1-(toluene-4-sulfonyl)piperidin-2-yl]propan-1-ol 
• 616866-58-1 (R)-4-[(S)-5-methylene-1-(toluene-4-sulfonyl)piperidin-2-yl]pent-2-enoic acid ethyl ester 

Relevant academic research and scientific papers

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.

A Concise Asymmetric Route to Nuphar Alkaloids. A Formal Synthesis of (-)-Deoxynupharidine

(Equation presented) A stereocontrolled route to Nuphar alkaloids is described that employs a formal [3 + 3] cycloaddition strategy to assemble the piperidine nucleus. The addition of Pd-TMM complexes to aziridine 10 was found to be sluggish; however, the addition of a functionalized allyl Grignard reagent followed by a Mitsunobu condensation reaction provided 11 in high yield. The employment of this route in the formal synthesis of (-)-deoxynupharidine 1 is described.