Synthesis of C-1 indol-3-yl substituted tetrahydroisoquinoline

Isoquinoline Alkaloids Chemistry and Pharmacology - Maurice

Det har varit en viktig reaktion inom alkaloid och organisk syntes sedan starten, där den har använts i utvecklingen av många beta-karboliner . Here we introduce a Pictet-Spengler ligation that is based on the classic Pictet-Spengler reaction of aldehydes and tryptamine nucleophiles. The ligation exploits the bioorthogonal reaction of aldehydes and alkoxyamines to form an intermediate oxyiminium ion; this intermediate undergoes intramolecular C–C bond formation with an indole nucleophile to form an oxacarboline product that is hydrolytically stable. Se hela listan på openwetware.org A novel vinylogous Pictet–Spengler cyclization has been developed for the generation of indole‐annulated medium‐sized rings. The method enables the synthesis of tetrahydroazocinoindoles with a fully substituted carbon center, a prevalent structural motif in many biologically active alkaloids. The strategy has been applied to the total synthesis of Die Pictet-Spengler-Reaktion ist eine chemische Reaktion zur Herstellung von Heterocyclen.

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Usually an acidic catalyst is employed and the reaction mixture heated, [1] [2] but some reactive compounds give good yields even at physiologic conditions. [3] The Pictet–Spengler (PS) reaction constructs many important phytochemicals such as morphine and camptothecin, but it has not yet been noticed in the fungal kingdom. Here, the startup of the PS reaction-based silent fungal biosynthetic machinery is presented to generate unforeseeably “unnatural” natural products of unprecedented carbon skeletons with antibacterial and acetylcholinesterase A catalytic asymmetric Pictet−Spengler reaction has been developed, wherein treating substituted tryptamines with an aldehyde in the presence of a catalytic amount of a chiral phosphoric acid provides the corresponding tetrahydro-β-carboline derivatives in high yields and enantiomeric excesses. The reaction works well with both aliphatic and aromatic aldehydes. Superacid-catalyzed Pictet-Spengler reactions of imines of 2-phenethylamine are presented, including the prototype Pictet-Spengler reaction of PhCH2CH2N:CH2 (I) to give the parent and 1-substituted 1,2,3,4-tetrahydroisoquinolines in moderate-to-high yields.

Pictet – Spengler-reaktion Kemi Natriumhydroxid Dimetylformamid

doi: 10.1021/bc400042a. Epub 2013 Jun 3.

tryptofol — Engelska översättning - TechDico

The Swiss chemists Amé Pictet and Theodor Spengler discovered for the first time that treatment of 2-phenylethanamine 1 and formaldehyde dimethylacetal 2 under acidic condition leads to the formation of 1,2,3,4-tetrahydroisoquinoline 3 (Scheme 1). The condensation discovered by Pictet and Spengler is the most important method for the synthesis of alkaloid scaffolds.

中文名. 皮克特－施彭格勒反应.
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[4] 1944 年 Sch瀀昀 等也发现高度活性的羟基取代的芳环可使 Pictet–Spengler 反应在温和的接近生理的条件下进行。. 中文名. 皮克特－施彭格勒反应. 外文名.

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tryptofol — Engelska översättning - TechDico

Previous Lewis acid catalyzed Pictet−Spengler reactions of unactivated ketones typically require two separate reactions (imine formation, cyclization) to obtain the same results An endohedrally functionalized self‐assembled Fe 4 L 6 cage complex can catalyze oxa‐Pictet—Spengler cyclizations of tryptophols and various aldehyde derivatives, showing strong rate accelerations and size‐selectivity.