2826-79-1

Upstream product

• 853925-56-1 2,3,5,6-tetrahydropyrrolo[2,1-a]isoquinoline 
• 172162-63-9 (1S,2R,10bS)-1,2-Bis<oxy>-1,2,3,5,6,10b-hexahydropyrrolo<2,1-a>isoquinolin-3-one 
• 164736-96-3 (1S,2R,10bS)-1,2-dihydroxy-1,2,3,5,6,10bβ-hexahydropyrrolo<2,1-a>isoquinolin-3(2H)-one 
• 341544-03-4 (E)-3-[(1R)-1,2,3,4-tetrahydroisoquinol-1-yl]-1-[(1R,2R)-2-hydroxy-1,2-dicyclohexylethyl]oxy-1-propene 
• 341544-29-4 (R)-1-(3-hydroxypropyl)-1,2,3,4-tetrahydroisoquinoline tert-butyl carbamate 
• 3230-65-7 3,4-dihydroisoquinoline 
• 496910-19-1 2-[(S)-2-((R)-1-Allyl-5,8-dibromo-1H-isoquinolin-2-yl)-1-methyl-2-oxo-ethyl]-isoindole-1,3-dione 
• 496910-21-5 1,2-dihydro-1-(R)-(3-hydroxypropyl)-2-[N-phthaloyl-(S)-alanyl]isoquinoline 
• 496910-20-4 5,8-dibromo-1,2-dihydro-1-(R)-(3-hydroxypropyl)-2-[N-phthaloyl-(S)-alanyl]isoquinoline 
• 496910-22-6 1,2,3,4-tetrahydro-1-(R)-(3-hydroxypropyl)-2-[N-phthaloyl-(S)-alanyl]isoquinoline 
• 81045-39-8 5,8-dibromoisoquinoline 
• 3327-29-5 1,2,3,5,6,10b-hexahydropyrrolo<2,1-a>isoquinoline 
• 496910-23-7 1,2,3,4-tetrahydro-1-(R)-(3-hydroxypropyl)isoquinoline 

Relevant academic research and scientific papers

A template-based mnemonic for monoamine oxidase (MAO-N) catalyzed reactions and its application to the chemo-enzymatic deracemisation of the alkaloid (±)-crispine A

A template-based mnemonic has been developed for the enzyme monoamine oxidase from Aspergillus niger and has been used to successfully identify the alkaloid (±)-crispine A as a target for chemo-enzymatic deracemisation yielding the biologically active (R)

The synthesis of isoquinoline alkaloid and its related compounds using alanine derivatives as chiral auxiliaries.

Chiral 1-substituted isoquinoline derivatives, which were obtained by the reaction using alanine derivatives as chiral auxiliaries, were transformed to (S)-2,3,9,10,11-pentamethoxyhomoprotoberberine (7) and a synthetic intermediate for O-methylkreysigine

Concise syntheses of harmicine and a pyrrolidino-isoquinoline derivative using chiral 1-allyl adducts of β-carboline and isoquinoline as starting materials

Total syntheses of (S)-harmicine and (R)-1,2,3,5,6,10b-hexahydropyrrolo[2,1-a]isoquinoline were carried out using chiral 1-allyl-1,2,3,4-tetrahydro-β-carboline and 1-allyl-1,2-dihydroisoquinoline as starting materials, respectively.

An allyltitanium derived from acrolein 1,2-dicyclohexylethylene acetal and (η2-propene)Ti(o-i-Pr)2 as a chiral propionaldehyde homoenolate equivalent that reacts with imines with excellent stereoselectivity. An efficient and practical access to optically active γ-amino carbonyl compounds

A chiral allyltitanium compound 2, prepared in situ by the reaction of optically active acrolein 1,2-dicyclohexylethylene acetal (3) with (η2-propene)Ti(O-i-Pr)2 (1), reacts with a variety of acyclic and cyclic imines 4 in a regiospecific way to afford α-addition products 5 as a mixture of the E- and Z-isomers in good combined yield, where the former is predominant in a ratio of 92: 8 to >95:5. The mixture of (E)- and (Z)-5 and pure (E)-5 which could be isolated in several cases were respectively converted to the corresponding β-amino ester 6 to confirm the absolute configuration and enantiomeric purity. The ee of the newly formed asymmetric center of 5 is more than 78% for the mixture of (E)- and (Z)-5 and more than 96% for pure (E)-5. By taking advantage of the versatility of the vinyl ether moiety in 5, optically active γ-amino aldehydes 8, γ-amino aldehyde acetals 7 and 10, γ-amino acids 9, β-amino esters 6, and pyrrolidinoisoquinolines 12 were readily prepared. In the reaction of 2 with optically active α-silyloxyimine 4n, remarkable double stereodifferentiation was observed; thus, the reaction of 2 derived from (S,S)- or (R,R)-3 provided syn- and anti-5n in a ratio of 55:45 or 0:100, respectively. Meanwhile, the stereochemistry of the product in the reaction of 2 with β-silyloxyimine 4o was controlled mainly by 2. Thus, the reaction of β-silyloxyimine 14 with 2 derived from 1 and (R,R)-3 afforded γ-silyloxyimine 15 with 92% diastereoselectivity, from which 4-amino6-hydroxypentadecanal dimethyl acetal (13), a key intermediate for the synthesis of batzelladine D, was synthesized.

Asymmetric Synthesis of Both Enantiomers of Pyrrolidinoisoquinoline Derivatives from L-Malic Acid and L-Tartaric Acid

The pyrrolidinoisoquinoline derivatives ((-)-3, (-)-4) and their antipodes ((+)-3, (+)-4) were prepared by reductive deoxygenation and reduction from the intermediates 9 and 10.The key intermediates 9 and 10 were prepared by a diastereoselective N-acyliminium ion cyclization of chiral lactams, which derived from L-malic acid and L-tartaric acid, respectively.