959051-08-2

Upstream product

• 1119-46-6 5-chloro-valeric acid 
• 1575-61-7 5-Chlorovaleroyl chloride 
• 108-95-2 phenol 

Downstream Products

• 1315314-33-0 C₂₀H₃₁Cl₂NO₃S 
• 1315314-30-7 (+)-(2R,3S)-7-chloro-2-(3-chloro-propyl)-3-((S)-2-methyl-propane-2-sulfinylamino)-heptanoic acid phenyl ester 
• 1315314-32-9 (-)-(1R,9aS)-octahydro-quinolizine-1-carboxylic acid phenyl ester 
• 1315314-36-3 (+)-(1S,9aS)-octahydro-quinolizine-1-carboxylic acid phenyl ester 
• 1315314-31-8 (-)-(8R,8aS)-octahydro-indolizine-8-carboxylic acid phenyl ester 
• 111975-29-2 (-)-tashiromine 
• 1451214-11-1 (2R,3S,E)-phenyl 2-(3-chloropropyl)-3-((S)-1,1-dimethylethylsulfinamido)-6-(trimethylsilyl)hex-4-enoate 
• 1451214-13-3 (2S,3R)-phenyl 1-allyl-2-((E)-3-(trimethylsilyl)prop-1-en-1-yl)piperidine-3-carboxylate 

Relevant academic research and scientific papers

Total synthesis of the tetracyclic lupin alkaloid (+)-allomatrine

(+)-Allomatrine (1) has been synthesized using an imino-aldol reaction and N-acyliminium cyclization as key steps. Strategically, use of the tert-butylsulfinimine derivative of (E)-4-(trimethylsilyl)but-2-enal enabled the staged formation of three C-C bon

Total syntheses of (-) epilupinine and (-)-tashiromine using imino-aldol reactions

Short routes to enantiomerically pure indolizidine and quinolizidine alkaloids have been developed using imino-aldol reactions of enolates derived from phenyl 5-chlorovalerate. High levels of syn selectivity (dr ～13-16:1) were obtained using lithium enolates of phenyl esters in combination with tert-butylsulfinyl imines. The imino-aldol adducts were deprotected and cyclized to afford (-)-epilupinine ((-)-2) and (-)-tashiromine ((-)-1) in two further steps.