First Total Synthesis of the Proposed Structures of Orisuaveolines A and B

Zhang, Jie; Da, Shijun; Xu, Feng; Chen, Xiaoyi; Jiang, Jianhui; Liu, Ying

doi:10.1002/cjoc.201200986

Cited by 12 publications

(3 citation statements)

References 14 publications

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“…Li and co‐workers reported the first total synthesis of β‐indoloquinazoline alkaloids Orisuaveloine A 158 and Orisuaveloine B 160 . The synthesis started with the reaction of tryptamine derivatives ( 155 a or 155 b ) with triphosgene in the presence of triethylamine to generate isocyanate in‐situ , which underwent intramolecular nucleophilic substitution in the presence of hydrogen bromide catalyst to provide tetrahydro‐β‐carboline‐1‐one ( 156 a or 156 b ) (Scheme ).…”

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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“…More quantitative models use the Eigen-Tamm formulation to quantify the association of ion pairs in both solvent-separated ion-pairs and contact ion-pairs. [10,11] The most-studied lyotropic biochemical effects involve the salting-in and salting-out of proteins to determine chaotropic and cosmotropic characteristics of ions, but the effects also apply to GAGs, mucins, and other proteoglycans. Studies of the water-air interface, Jones-Dole viscosity B Coefficients for biopolymer, and effects such as arginine-arginine pairing have revealed that models of point-charge electrostatics fail…”

Section: Background: Ion-specific Behavior or Lyotropymentioning

confidence: 99%

A Continuum Model of Mucosa with Glycan‐Ion Pairing

Sterling

Baker

2018

Macro Theory & Simulations

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Advances in the study of glycosoaminoglycan biohydrogels, label‐free electrokinetic analysis of soft‐diffuse layers in contact with saline solutions, and elucidation of ion‐specific behavior in many biochemical systems offer the opportunity to marry these principal features in a new mathematical model of the mucosal glycocalyx. The model is based on the electroquasistatic subset of Maxwell's equations in the form of the steady‐state continuum Poisson–Boltzmann equation for electrostatics with explicit incorporation of pairwise binding of ions to fixed charged‐groups in the hydrogel. The pairwise association is modeled using reversible bimolecular reactions via stoichiometric dissociation constants that represent the rule of matching water affinities—the observation that similar hydration structures of the pair results in less dissociation. Applications of the model to specific gels and salts, including a heparin star polyethylene glycol (starPEG) biohydrogel and the airway surface liquid layer in cystic fibrosis, are presented to postulate some quantitative consequences of glycocalyx ion partitioning.

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“…One is acid promoted Fischer indole synthesis from the corresponding hydrazone intermediates . The other is condensation of tryptamine derivatives with hazardous triphosgene or chloroformates followed by acid promoted Friedel–Crafts acylation . Recently, transition-metal-catalyzed cyclizations have also been reported for the synthesis of these scaffolds to avoid harsh reaction conditions and multistep syntheses …”

Section: Introductionmentioning

confidence: 99%