414871-53-7

Upstream product

• 72659-59-7 lithium R-(-)-N-isopropyl-1-phenylethyl amide 
• 268541-14-6 N-benzyl-N-(1-methyl-1-phenylethyl)-4-methoxybenzamide 
• 100-07-2 4-methoxy-benzoyl chloride 
• 454479-63-1 N-(1-methyl-1-phenylethyl)-4-methoxybenzamide 
• 585-32-0 2-phenyl-2-propylamine 

Downstream Products

• 1293306-05-4 C₂₉H₄₁NO₂Si₂ 
• 1293306-08-7 (3S,3aS,7S,7aR)-3-phenyl-7-(trimethylsilyl)hexahydro-1H-isoindole-1,5(6H)-dione 
• 1293305-94-8 tert-butyl (1S,3aR,4S,7aS)-3,6-dioxo-1-phenyl-4-(trimethylsilyl)hexahydro-1H-isoindole-2(3H)-carboxylate 
• 1293305-93-7 (3S,3aS,7S,7aR)-3-phenyl-2-(2-phenylpropan-2-yl)-7-(trimethylsilyl)hexahydro-1H-isoindole-1,5(6H)-dione 
• 454479-66-4 (1S,3aR,4S,7aS)-4-methyl-3,6-dioxo-1-phenyl-octahydro-isoindole-2-carboxylic acid tert-butyl ester 
• 454479-65-3 (3S,3aS,7S,7aR)-7-methyl-3-phenylperhydro-isoindole-1,5-dione 
• 487-79-6 (-)-kainic acid 
• 848476-35-7 (1R,3aS,4R,7aR)-2-tert-butyl 1-methyl hexahydro-4-((3-tert-butyldiphenylsilyloxy)propyl)-3,6-dioxo-1H-isoindole-1,2(3H)-dicarboxylate 
• 848476-33-5 (1R,3aS,4R,4aR)-tert-butyl hexahydro-3,6-dioxo-1-phenyl-1H-isoindole-4-(3-formyloxypropyl)-3(3H)-carboxylate 
• 848476-42-6 3-((3R,3aR,7R,7aS)-octahydro-1,5-dioxo-3-phenyl-1H-isoindol-7-yl)propyl formate 
• 848476-32-4 (3R,3aR,7R,7aS)-hexahydro-7-(1-triisopropylsilyloxy)propyl-3-phenyl-2-(2-phenylpropan-2-yl)-6H-isoindole-1,5-dione 

Relevant academic research and scientific papers

A general synthetic approach to the amnesic shellfish toxins: Total synthesis of (-)-isodomoic acid B, (-)-isodomoic acid E and (-)-isodomoic acid F

The alkynylpyrrolidine 4 was made via a dearomatising cyclisation of an aromatic amide, and was elaborated by stannylcupration and palladium-catalysed coupling to achieve the first total synthesis of three members of the isodomoic acid family; the same alkyne can be envisaged as a precursor to several more of this class of amnesic shellfish toxins. The Royal Society of Chemistry.

The synthesis of (-)-isodomoic acid C

The neuroactive algal metabolite (-)-isodomoic acid C, a kainoid amino acid, has been synthesized for the first time. Asymmetric dearomatizing cyclization of an aromatic amide using a chiral lithium amide base generates a bicyclic enone containing a pyrro

Synthesis of (-)-kainic acid using chiral lithium amides in an asymmetric dearomatizing cyclization

Chiral lithium amide bases are able to deprotonate N-benzyl-N-cumyl anisamides enantioselectively to yield enantiomerically enriched benzylic organolithiums. These spontaneously undergo dearomatising cyclisation to yield, in high enantiomeric excess enantiomerically enriched partially saturated isoindolones, which in some cases may be recrystallised to enantiomeric purity. These isoindolone derivatives are converted in nine steps, among them a surprisingly regioselective Baeyer-Villiger reaction, to (-)-kainic acid.