72504-66-6

Upstream product

• 5096-11-7 (R)-1-(3-pyridyl)ethanol 
• 100-44-7 benzyl chloride 
• 350-03-8 methyl-3-pyridylketone 
• 4754-27-2 1-(3-Pyridyl)ethanol 
• 27854-86-0 (1R)-1-(3-pyridyl)ethyl acetate 

Downstream Products

• 183866-61-7 5-((R)-1-Hydroxy-ethyl)-3,6-dihydro-2H-pyridine-1-carboxylic acid benzyl ester 
• 189288-87-7 (1S,4aR,11R,11aS)-2-Benzyl-1-cyano-11-methyl-1,2,3,4,4a,5,11,11a-octahydro-pyrido[4,3-b]carbazole-6-carboxylic acid tert-butyl ester 
• 189288-86-6 (3Z,4R)-1-benzyl-3-ethylidene-4-(2-indolylmethyl)piperidine 
• 183866-66-2 (R)-3-Eth-(Z)-ylidene-4-(1H-indol-2-ylmethyl)-piperidine-1-carboxylic acid benzyl ester 
• 183866-63-9 (R,Z)-benzyl 3-ethylidene-4-(2-methoxy-2-oxoethyl)piperidine-1-carboxylate 
• 189288-85-5 [(R)-1-Benzyl-3-eth-(Z)-ylidene-piperidin-4-yl]-acetic acid methyl ester 

Relevant academic research and scientific papers

Total syntheses of the Strychnos indole alkaloids (-)-tubifoline, (-)-tubifolidine, and (-)-19,20-dihydroakuammicine

Two different strategies for the synthesis of pentacyclic Strychnos alkaloids in enantiomerically pure form are explored. Both of them involve the use of enantiopure 2-(4-piperidylmethyl)indoles prepared by kinetic resolution of 1-(3-pyridyl)ethanol, followed by partial reduction of the pyridine ring to the tetrahydropyridine level, Claisen rearrangement of the resulting allylic alcohol, and finally Smith indolization. Whereas 2-(4-piperidylmethyl)indole 6 could not be converted to tetracyclic ABDE substructures of Strychnas alkaloids, photocyclization of chloroacetamide 14, derived from (piperidylmethyl)indole 13, satisfactorily afforded the stemmadenine-type tetracycle 15, which was then converted to the alkaloids (-)-tubifoline, (-)-tubifolidine, and (-19,20-dihydroakuammicine.

An enantioselective synthesis of the Strychnos alkaloid (-)-tubifoline

An enantioselective synthesis of the Strychnos alkaloid (-)-tubifoline, involving the kinetic resolution of racemic 1-(3-pyridyl)ethanol, the orthoester Claisen rearrangement of the enantiopure allylic alcohol 5, Smith indolization of the resulting 4-piperidineacetate 6, photocyclization of chloroacetamide 9, and final transannular cyclization, is reported.