139407-08-2

Upstream product

• 487-79-6 (-)-kainic acid 

Downstream Products

• 487-79-6 (+/-)-α-kainic acid 
• 103314-33-6 (2S,3S,4S)-3-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-(tert-butyl-dimethyl-silanyloxymethyl)-4-{(E)-4-oxo-1-[phenylsulfanyl-(2,2,2-trifluoro-acetoxy)-methyl]-pent-2-enyl}-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 103314-32-5 (2S,3S,4S)-4-((E)-1-Benzenesulfinylmethyl-4-oxo-pent-2-enyl)-3-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2-(tert-butyl-dimethyl-silanyloxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 103314-31-4 (2S,3S,4S)-3-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-(tert-butyl-dimethyl-silanyloxymethyl)-4-((E)-4-oxo-1-phenylsulfanylmethyl-pent-2-enyl)-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 115268-37-6 (2S,3S,4S)-4-((Z)-1-Acetyl-4-phenylsulfanyl-but-1-enyl)-3-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2-(tert-butyl-dimethyl-silanyloxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 103314-30-3 (2S,3S,4S)-3-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-(tert-butyl-dimethyl-silanyloxymethyl)-4-(1-formyl-2-phenylsulfanyl-ethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 86630-10-6 acromelic acid B 
• 86630-09-3 Acromelic acid A 
• 487-79-6 (-)-kainic acid 

Relevant academic research and scientific papers

Synthesis of kainoids via a highly stereoselective hydroformylation of kainic acid

An efficient preparation of a series of secondary amines, structurally related to the kainic acid scaffold, is described. Naturally occurring (-)-α-kainic acid was hydroformylated with complete terminal selectivity and high stereoselectivity. The stereoch

Parallel synthesis of novel heteroaromatic acromelic acid analogues from kainic acid

A range of new C-4 heteroaromatic acromelic acid analogues has been synthesized in a parallel fashion from (-)-α-kainic acid 1. Protection of the amine and carboxylate groups of 1 followed by ozonolysis gave methyl ketone 8. A silyl enol ether 9, generated regiospecifically from the methyl ketone 8 using "kinetic" conditions, was brominated in situ with phenyltrimethylammonium perbromide to give the key α-bromo ketone 10. Parallel cyclization reactions of bromo ketone 10 with thioamides and thioureas were then performed. The aromatic heterocyclic derivatives 11a-d and 19 produced were deprotected to give the new kainoid amino acids 6a-d and 25 in excellent yield. Compounds 6a and 6c show strong binding to the kainate receptor. Reaction of 10 with alternative condensing agents was also briefly investigated.

Palladium-Catalysed Vinylic Substitution of Dimethyl Esters of N-Alkoxycarbonylkainic Acids with Aryl Halides

The palladium-catalysed reaction of dimethyl esters of N-alkoxycarbonylkainic acids with aryl halides in the presence of catalytic amounts of Pd(OAc)2 and of the n-Bu4NCl/NaHCO3 combination affords stereoselectively the co

SYNTHESIS OF ACROMELIC ACID A, A TOXIC PRINCIPLE OF CLITOCYBE ACROMELALGA.

Acromelic acid A, a toxic principle of Clitocybe acromelalga, was synthesized from L-α-kainic acid.The synthesis established the previously inferred structure, and determined the absolute configuration as shown by 1.