Journal ArticleDOI
Nitrogen heterocycles by palladium-catalyzed cyclization of amino-tethered vinyl halides and ketone enolates.
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The scope and limitations of Pd(0)-catalyzed intramolecular coupling of amino-tethered vinyl halides and ketone enolates as a methodology for the synthesis of nitrogen heterocycles have been studied.Abstract:
The scope and limitations of Pd(0)-catalyzed intramolecular coupling of amino-tethered vinyl halides and ketone enolates as a methodology for the synthesis of nitrogen heterocycles have been studied. This reaction constitutes a synthetic procedure to obtain bridged, condensed, and monocyclic nitrogen-containing compounds.read more
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Large-scale applications of transition metal-catalyzed couplings for the synthesis of pharmaceuticals.
Javier Magano,Joshua R. Dunetz +1 more
Journal ArticleDOI
Collective synthesis of natural products by means of organocascade catalysis
TL;DR: It is shown that the application of two nature-inspired techniques, namely organocascade catalysis and collective natural product synthesis, can facilitate the preparation of useful quantities of a range of structurally diverse natural products from a common molecular scaffold.
Journal ArticleDOI
Total Synthesis of the Strychnos Alkaloid (+)-Minfiensine: Tandem Enantioselective Intramolecular Heck–Iminium Ion Cyclization
TL;DR: A cascade catalytic asymmetric Heck-iminium cyclization was developed that rapidly provides 3,4-dihydro-9a,4a-(iminoethano)-9H-carbazoles in high enantiomeric purity and uses palladium-catalyzed reactions to form all carbon-carbon bonds in the transformation of these simple precursors to (+)-minfiensine.
Journal ArticleDOI
Total Synthesis of (±)-Aspidophylline A
TL;DR: The route features a number of key transformations, including a Heck cyclization and a late-stage interrupted Fischer indolization to install the furoindoline and construct the natural product's pentacyclic framework.
Journal ArticleDOI
Total synthesis of (+/-)-strychnine via a [4 + 2]-cycloaddition/rearrangement cascade.
TL;DR: A new strategy for the synthesis of the Strychnos alkaloid (+/-)-strychnine has been developed and is based on an intramolecular [4 + 2]-cycloaddition/rearrangement cascade of an indolyl-substituted amidofuran.
References
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Journal ArticleDOI
A Short, Stereocontrolled Synthesis of Strychnine
Viresh H. Rawal,Seiji Iwasa +1 more
TL;DR: Strychnine has been synthesized by a short, highly stereocontrolled route that involves the efficient transformation of commercially available 2-nitrophenylacetonitrile into isostrychnin, a known precursor to strychnines.
Journal ArticleDOI
Catalytic asymmetric vinylation of ketone enolates.
TL;DR: A protocol for the catalytic asymmetric vinylation of ketone enolates has been developed and key to the success of this process was the development of new electron-rich chiral monodentate ligands.
Journal ArticleDOI
A General Synthetic Entry to Strychnos Alkaloids of the Curan Type via a Common 3a-(2-Nitrophenyl)hexahydroindol-4-one Intermediate. Total Syntheses of (±)- and (−)-Tubifolidine, (±)-Akuammicine, (±)-19,20-Dihydroakuammicine, (±)-Norfluorocurarine, (±)-Echitamidine, and (±)-20-Epilochneridine1
TL;DR: In this paper, a general strategy for the synthesis of pentacyclic Strychnos alkaloids with the curan skeleton has been developed, which utilizes 3a-(2-nitrophenyl)hexahydroindol-4-one (23), which was prepared from 2-allyl-2-2-(1,3-cyclohexanedione (15), as the common, pivotal intermediate.
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