183866-63-9

Upstream product

• 1445-45-0 Trimethyl orthoacetate 
• 183866-61-7 5-((R)-1-Hydroxy-ethyl)-3,6-dihydro-2H-pyridine-1-carboxylic acid benzyl ester 
• 72504-66-6 (1R)-1-(1-benzyl-1,2,5,6-tetrahydro-3-pyridyl)ethanol 
• 501-53-1 benzyl chloroformate 
• 350-03-8 methyl-3-pyridylketone 
• 4754-27-2 1-(3-Pyridyl)ethanol 
• 5096-11-7 (R)-1-(3-pyridyl)ethanol 
• 27854-86-0 (1R)-1-(3-pyridyl)ethyl acetate 

Downstream Products

• 183866-66-2 (R)-3-Eth-(Z)-ylidene-4-(1H-indol-2-ylmethyl)-piperidine-1-carboxylic acid benzyl ester 
• 6474-90-4 tetrahydroalstonine 
• 483-04-5 ajmalicine 

Relevant academic research and scientific papers

ENANTIOSELECTIVE SYNTHESES OF HETEROYOHIMBINE NATURAL PRODUCT INTERMEDIATES

Enantioselective syntheses of cis- and trans-bicyclic dihydropyran compounds, and other intermediates, en route to heteroyohimbine alkaloids.

Enantioselective syntheses of heteroyohimbine natural products: A unified approach through cooperative catalysis

Alstonine and serpentine are pentacyclic indoloquinolizidine alkaloids (referred to as "anhydronium bases") containing three contiguous stereocenters. Each possesses interesting biological activity, with alstonine being the major component of a plant-based remedy to treat psychosis and other nervous system disorders. This work describes the enantioselective total syntheses of these natural products with a cooperative hydrogen bonding/enamine-catalyzed Michael addition as the key step. The enantioselective total syntheses of the natural products alstonine and serpentine are presented. They proceed through a sequence with a cooperative hydrogen bonding/enamine-catalyzed Michael addition as the key step.

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.