Synthesis of Tetracyclic Tetrahydro‐β‐carbolines by Acid‐Promoted One‐Pot Sequential Formation of C−C and C−N Bonds

Nagaraju, V.; Purnachander, Dalovai; Goutham, Kommuru; Suresh, Surisetti; Sridhar, Balasubramanian; Karunakar, Galla V.

doi:10.1002/ajoc.201600349

Cited by 14 publications

(2 citation statements)

References 86 publications

(13 reference statements)

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“…In 2016, Nagaraju et al. reported a one‐pot synthetic approach to access tetracyclic tetrahydro‐β‐carboline fused γ‐lactam framework . As illustrated in Scheme , the β‐enaminone derivative of tryptamine 95 and acetylene‐dicarboxylate 96 derivatives were dissolved in acetonitrile and heated in the presence of one equivalent of anhydrous p ‐TSA afford the corresponding tetracyclic derivative 98 in 51–77% yields.…”

Section: β‐Carboline Fused Heterocycles Synthesized Via Post‐pictet‐smentioning

confidence: 99%

Post‐Pictet‐Spengler Cyclization (PPSC): A Strategy to Synthesize Polycyclic β‐Carboline‐Derived Natural Products and Biologically Active N‐Heterocycles

Singh

Kumar

Patil³

et al. 2020

Adv Synth Catal

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Pictet-Spengler reaction is a typical condensation reaction of β-arylethylamine or Tryptamine with an aldehyde or ketone followed by ring closure to generate tetrahydroisoquinoline (THIQ) and Tetrahydro-β-carboline (THβC), respectively. Both these key skeletons represent huge range of structurally diverse naturally occurring isoquinoline and indole alkaloids. Nature has synthesized structurally complex Reserpine, Ajmalicine as well as other related alkaloids using various biosynthetic pathways via Pictet-Spengler reaction followed by post-Pictet-Spengler cyclization (PPSC) stratergy. This biosynthetic process is the short and reliable method to access diverse range of polycyclic heterocycles. Over the period of last sixty years, several researchers have synthesized complex alkaloids without highlighting the synthetic utility of the post-Pictet-Spengler cyclization strategy. We summarized the synthesis of numerous natural products and related natural product inspired heterocyclic scaffolds which follow the PPSC strategy to demonstrate its usefulness for the construction of diverse compound collection.

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Section: β‐Carboline Fused Heterocycles Synthesized Via Post‐pictet‐smentioning

confidence: 99%

Post‐Pictet‐Spengler Cyclization (PPSC): A Strategy to Synthesize Polycyclic β‐Carboline‐Derived Natural Products and Biologically Active N‐Heterocycles

Singh

Kumar

Patil³

et al. 2020

Adv Synth Catal

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“…Recently, in the year 2016, Karunakar et al have demonstrated the tetrahydro-β-carboline derivatives via an acid mediated one-pot sequential formation of C–C and C–N bond . The Scheme shows the reaction of β-enaminone 211 and acetylenedicarboxylate 212 using p -TSA as an acid catalyst at 70 °C for 3 h to obtain the tetrahydro-β-carboline derivatives 213 .…”

Section: Multicomponent Synthetic Approach For the Synthesis Of Tetra...mentioning

confidence: 99%

Application of Pictet–Spengler Reaction to Indole-Based Alkaloids Containing Tetrahydro-β-carboline Scaffold in Combinatorial Chemistry

2017

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Indole-based alkaloids are well-known in the literature for their diverse biological properties. Polysubstituted optically active tetrahydro-β-carboline derivatives functionalized on C-1 position are the common structural motif in most of the indole-based alkaloids, as well as highly marketed drugs. The stereoselective Pictet-Spengler reaction is one of the currently most important synthetic techniques used for the preparation of these privileged tetrahydro-β-carboline scaffolds. To date, there are numerous research reports that have been published on the synthesis of the tetrahydro-β-carboline scaffold both on solid phase, as well as in solution phase. Moreover rapid growth has been observed for the enantioselective synthesis of tetrahydro-β-carboline scaffold using chiral organocatalysts. In this Review, efforts have been taken to shed light on the latest information available on different strategies to synthesize tetrahydro-β-carboline both on solid phase and in solution phase during the last 20 years. Furthermore, we believe that the present synthetic methodologies covered in this Review will help to improve the status of this privileged tetrahydro-β-carboline scaffold in its use for drug discovery.

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Conversion of O‐Propargyl β‐enones to 2‐Allylidene 1,3‐Diones and Furan Derivatives via [3,3]‐Sigmatropic Rearrangement

et al. 2019

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Synthesis of Tetracyclic Tetrahydro‐β‐carbolines by Acid‐Promoted One‐Pot Sequential Formation of C−C and C−N Bonds

Cited by 14 publications

References 86 publications

Post‐Pictet‐Spengler Cyclization (PPSC): A Strategy to Synthesize Polycyclic β‐Carboline‐Derived Natural Products and Biologically Active N‐Heterocycles

Post‐Pictet‐Spengler Cyclization (PPSC): A Strategy to Synthesize Polycyclic β‐Carboline‐Derived Natural Products and Biologically Active N‐Heterocycles

Application of Pictet–Spengler Reaction to Indole-Based Alkaloids Containing Tetrahydro-β-carboline Scaffold in Combinatorial Chemistry

Conversion of O‐Propargyl β‐enones to 2‐Allylidene 1,3‐Diones and Furan Derivatives via [3,3]‐Sigmatropic Rearrangement

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