Stereoselective synthesis of (+)-(8R,8aR)-perhydro-8-indolizidinol

Kumar, R. Sateesh Chandra; Reddy, G. Venkateswar; Babu, K. Suresh; Rao, J. Madhusudana

doi:10.1016/j.tetlet.2011.05.102

Cited by 7 publications

(6 citation statements)

References 34 publications

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“…Carbon–nitrogen bonds in several relatively simple 2-substituted piperidine natural products, specifically (−)-andrachcinidine, (+)-β-conhydrine, (+)-deoxocassine, (+)-perhydro-8-indolizidinol, and (−)-deoxoprosophylline were established by the reaction of different linear sulfonate precursors with sodium azide. In this series, the total synthesis of (−)-epiquinamide A, a nicotinic agonist in central nervous system (CNS) disorders, examplifies the stereoselective installation of both C–N bonds of the alkaloid using the azidolysis strategy (Scheme ).…”

Section: Stereoselective Formation Of C–n Bonds By Nucleophilic Subst...mentioning

confidence: 99%

“…Similar amination reactions by nucleophilic substitution with sodium azide in fiveor sixmembered ring systems were utilized for the syntheses of (+)-nangustine, 190 (+)-febrifugine, 191 pachastrissamine (jaspine B), 192 dysiherbaine, 193 spicamycin, 194 and antitumor agent FR901464. 195 Carbon−nitrogen bonds in several relatively simple 2-substituted piperidine natural products, specifically (−)andrachcinidine, 196 (+)-β-conhydrine, 197 (+)-deoxocassine, 199 (+)-perhydro-8-indolizidinol, 198 and (−)-deoxoprosophylline 199 were established by the reaction of different linear sulfonate precursors with sodium azide. In this series, the total synthesis of (−)-epiquinamide A, a nicotinic agonist in central nervous system (CNS) disorders, examplifies the stereoselective installation of both C−N bonds of the alkaloid using the azidolysis strategy (Scheme 41).…”

Section: Stereoselective Formation Of C−n Bondsmentioning

confidence: 99%

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Cutting-Edge and Time-Honored Strategies for Stereoselective Construction of C–N Bonds in Total Synthesis

et al. 2016

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The main objective of this review is to provide a comprehensive survey of methods used for stereoselective construction of carbon-nitrogen bonds during the total synthesis of nitrogen-containing natural products that have appeared in the literature since 2000. The material is organized by specific reaction in order of decreasing number of applications in natural product synthesis. About 800 total syntheses of natural products with stereogenic carbon-nitrogen bonds described since 2000 have been reviewed.

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Section: Stereoselective Formation Of C–n Bonds By Nucleophilic Subst...mentioning

confidence: 99%

Section: Stereoselective Formation Of C−n Bondsmentioning

confidence: 99%

Cutting-Edge and Time-Honored Strategies for Stereoselective Construction of C–N Bonds in Total Synthesis

et al. 2016

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“…(Scheme 21) [277,279] Indoles addition by Friedel-Craft reaction: The reaction of indoles with unsaturated ketones and nitro styrenes using graphene oxide catalyst is performed by Rao and workers which in turn became one of the most efficient reaction in which a lewis acid was used as intermediate. (Scheme 22) [280,278] Scheme 19. G-SO 3 H catalyzed Pechmann condensation of resorcinol.…”

Section: Chemistryselectmentioning

confidence: 99%

Graphene‐based Composite Materials as Catalyst for Organic Transformations

et al. 2023

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Graphene is one of the most auspicious constituents in nanotechnology. It provides the most accurate theoretical 2‐D depiction of catalytic sustenance. Its exceptional, physico‐chemical, and mechanical qualities make it distinctive and also able to create composite materials with novel capabilities. Although using graphene as a single‐layered sheet as a catalytic tool has not been documented yet, certain encouraging outcomes using few‐layer graphene have previously been attained. We will quickly go through the most pertinent synthetic methods for obtaining graphene and graphene based materials in this article. The composites of graphene are used in various catalytic reactions, including Coupling reactions, Aza‐Michael addition, Hydration, Oxidation, Esterification, Pechmann Condensation, Knoevenagel Condensation, Ring‐Opening Polymerization, Friedel‐Crafts Addition, Ring Opening of Epoxides and Decarboxylation have been catalysed by these expertly crafted and prepared graphene‐based catalysts. The graphene based composites allows for easy, recyclable, arnold transform, and environmentally friendly photocatalysis and also mild, precise, and super effective conversions and synthesis.

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“…The intrinsic oxidability of GO imparts it the ability of catalyzing the oxidation reactions of hydrocarbons, cis ‐stilbene, benzyl alcohol,[7b], sulfides and thiols . Moreover, its inherent acidity allows it to catalyze the hydration of various alkynes,[7b],[12b] the ring opening of epoxy, Aza‐Michael additions, and Friedel–Crafts reactions . Lan et al reported the cycloaddition of carbon dioxide to propylene oxide for the synthesis of propylene carbonate using GO as catalyst and tetrabutylammonium bromide as cocatalyst…”

Section: Introductionmentioning

confidence: 99%

“…[ 15 ] Moreover, its inherent acidity allows it to catalyze the hydration of various alkynes, [ 7b , 12b ] the ring opening of epoxy, [ 16 ] Aza-Michael additions, [ 17 ] and Friedel-Crafts reactions. [ 18 ] Lan et al reported the cycloaddition of carbon dioxide to propylene oxide for the synthesis of propylene carbonate using GO as catalyst and tetrabutylammonium bromide as cocatalyst. [ 19 ] More recently, GO is also found effective in catalyzing polymerization reactions.…”

mentioning

confidence: 99%

Radical Chain Polymerization Catalyzed by Graphene Oxide and Cooperative Hydrogen Bonding

Zhu

Shi

Wang

2015

Macromol. Rapid Commun.

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Graphene oxide (GO) is effective in catalyzing a wide variety of organic reactions and a few types of polymerization reactions. No radical chain polymerizations catalyzed by GO have been reported. In this article, we probe the catalytic role and acceleration effect of GO for self-initiated radical chain polymerizations of acrylic acid (AA) in the presence of GO and a pre-existing polymer, poly(N-vinylpyrrolidone) (PVP), from a calorimetric perspective. Gelation experiments and DSC studies show that GO can function as a catalyst to accelerate the radical chain polymerization of AA. Isothermal polymerization kinetic data shows that the addition of GO diminishes the induction periods and increases the polymerization rates, as indicated by the much enhanced overall kinetic rate constants and lowered activation energies. The catalytic effect of GO for the polymerization of AA is attributed to the acidity of GO and the hydrogen bonding interactions between GO and monomer molecules and/or polymers.

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Stereoselective synthesis of (+)-(8R,8aR)-perhydro-8-indolizidinol

Cited by 7 publications

References 34 publications

Cutting-Edge and Time-Honored Strategies for Stereoselective Construction of C–N Bonds in Total Synthesis

Cutting-Edge and Time-Honored Strategies for Stereoselective Construction of C–N Bonds in Total Synthesis

Graphene‐based Composite Materials as Catalyst for Organic Transformations

Radical Chain Polymerization Catalyzed by Graphene Oxide and Cooperative Hydrogen Bonding

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