Cyclopropylazetoindolines as Precursors to C(3)-Quaternary-Substituted Indolines
Journal of the American Chemical SocietyPublished 2 June 2010
Vinson R. Espejo, Xi‐Bo Li, Jon D. Rainier
Citations81
SJR quartileQ1
SJR score5.55
SNIP2.61
Generate an AI Snapshot to get a quick, structured summary of this paper.
Study Snapshot
ObjectiveStudy objective
MethodsResearch methodology
PopulationPopulation studied
Sample sizeSample sizes
OutcomesStudy outcomes here
ResultsStudy results comes here
LimitationsResearch study limitations comes here
A concise AI-generated summary of the paper will appear here once you click Generate AI Snapshot.
Abstract
This manuscript describes the generation and use of a cyclopropylazetoindoline, a novel fused heterocycle, in coupling reactions with hetero- and carbon nucleophiles to give C(3)-quaternary-substituted pyrroloindolines.
Keywords
Chemistry
Chemical ReviewsDonor−Acceptor-Substituted Cyclopropane Derivatives and Their Application in Organic Synthesis
1,577 Citations2003Hans‐Ulrich Reißig, Reinhold Zimmer
Chemical ReviewsThe Asymmetric Intramolecular Heck Reaction in Natural Product Total Synthesis
1,471 Citations2003Amy B. Dounay, Larry E. Overman
TetrahedronRecent advances in donor–acceptor (DA) cyclopropanes
686 Citations2004Ming Yu, Brian L. Pagenkopf
European Journal of Organic ChemistryEnantioselective Catalytic Formation of Quaternary Stereogenic Centers
545 Citations2007Pier Giorgio Cozzi, Robert Hilgraf +1 more
TetrahedronStereoselective formation of quaternary carbon centers and related functions
494 Citations2003Irina Denissova, Louis Barriault
Proceedings of the National Academy of SciencesEnantioselective organocatalytic construction of pyrroloindolines by a cascade addition–cyclization strategy: Synthesis of (–)-flustramine B
464 Citations2004Joel F. Austin, Sung-Gon Kim +3 more
Angewandte Chemie International EditionTotal Synthesis of Complex Cyclotryptamine Alkaloids: Stereocontrolled Construction of Quaternary Carbon Stereocenters
459 Citations2007Alan Steven, Larry E. Overman
This review tells the story behind the development of this toolbox of synthetic methods, and their validation through the total synthesis of a number of structurally complex cyclotryptamine alkaloids, and highlights an aspect of asymmetric catalysis that has received little attention.
ScienceTotal Synthesis of (+)-11,11'-Dideoxyverticillin A
323 Citations2009Justin Kim, James A. Ashenhurst +1 more
This work reports a concise enantioselective total synthesis of (+)-11,11′-dideoxyverticillin A via a strategy inspired by the biosynthetic hypothesis for this alkaloid through a rapid functionalization of the advanced molecular framework.
Journal of the American Chemical SocietyTotal Synthesis of 5-<i>N</i>-Acetylardeemin and Amauromine: Practical Routes to Potential MDR Reversal Agents
247 Citations1999Kristopher M. Depew, Stephen P. Marsden +4 more
Using the methodology worked out for the titled compounds, a practical synthesis of several promising MDR reversal agents was possible and compounds 2, 50, and 51 were selected for more extensive biological follow-up.
Journal of the American Chemical SocietyTotal Synthesis of (±)-Psychotrimine
183 Citations2008Timothy R. Newhouse, Phil S. Baran
A new process for the union of anilines with tryptamine derivatives has been developed, furnishing C-3 quaternized pyrroloindoline architectures, and the complex natural product psychotrimine has been fashioned with a rare level of efficiency and practicality.
Journal of the American Chemical SocietyStereoselective Total Syntheses of Amauromine and 5-N-Acetylardeemin. A Concise Route to the Family of "Reverse-Prenylated" Hexahydropyrroloindole Alkaloids
173 Citations1994Stephen P. Marsden, Kristopher M. Depew +1 more
Journal of Biological ChemistryEpidithiodiketopiperazines Block the Interaction between Hypoxia-inducible Factor-1α (HIF-1α) and p300 by a Zinc Ejection Mechanism
161 Citations2009Kristina M. Cook, Stephen T. Hilton +4 more
Structural-activity studies employing both natural and synthetic ETP derivatives reveal that only the structurally unique ETP core is required and sufficient to block the interaction of HIF-1α and p300 and reveal that ETPs react with p300, causing zinc ion ejection.
The Journal of Organic ChemistryAsperazine, a Selective Cytotoxic Alkaloid from a Sponge-Derived Culture of <i>Aspergillus niger</i>
156 Citations1997Mustafa Varoglu, Thomas H. Corbett +2 more
Current Organic ChemistryEnantioselective Synthesis of Oxygen-, Nitrogen- and Halogen-Substituted Quaternary Carbon Centers
152 Citations2004Diego J. Ramón, Miguel Yus
ToxiconAbout the toxicity of some Strychnos species and their alkaloids
148 Citations2004Geneviève Philippe, Luc Angenot +2 more
By their nature, poisons such as strychnine and curare affect the functioning of the victim's body; this also means that they have been an important source of pharmacological tools and medicines all over the world.
Chemistry - A European JournalDiscovery through Total Synthesis: A Retrospective on the Himastatin Problem
112 Citations2001Theodore M. Kamenecka, Samuel J. Danishefsky
The outlines for a biological pharmacophore have been delineated and the alternating D- and L-substituents in the 6-mer as well as the biaryl linkage connecting the two identical subunits are critical for maintaining biological activity.
Organic LettersFacile and General Synthesis of Quaternary 3-Aminooxindoles
111 Citations2008Stephen P. Marsden, Emma Watson +1 more
Organic LettersFirst Total Synthesis of Trimeric Indole Alkaloid, Psychotrimine
102 Citations2007Yohei Matsuda, Mariko Kitajima +1 more
The first total synthesis of (+/-)-psychotrimine, a novel trimeric indole alkaloid isolated from Psychotria rostrata, was achieved.
Organic LettersMechanistic Insights into the Stereocontrolled Synthesis of Hexahydropyrrolo[2,3-<i>b</i>]indoles by Electrophilic Activation of Tryptophan Derivatives
85 Citations2007Carlos Silva López, Carlos Pérez‐Balado +2 more
A three-step mechanism involving the formation and rearrangement of an intermediate with indoline-azetidine spirocyclic core structure was shown by DFT computations to account for the electrophilic cyclization of tryptophan derivatives to hexahydropyrrolo[2,3-b]indoles.
Journal of the American Chemical SocietyAn Expeditious Synthesis of C(3)−N(1′) Heterodimeric Indolines
84 Citations2008Vinson R. Espejo, Jon D. Rainier
This paper describes the efficient and relatively simple synthesis of C(3)-N(1') heterodimeric indolines from the addition of indole nucleophiles to readily available bromopyrroloindolines.
Journal of the Chemical Society TransactionsXLII.—Physostigmine (eserine). Part III
83 Citations1925Edgar Stedman, George Barger
Organic LettersTotal Synthesis of Kapakahine E and F
70 Citations2010Vinson R. Espejo, Jon D. Rainier
The total synthesis of the cyclic peptides kapakahine E and F using bromopyrroloindoline heterodimerization reactions, indoline to alpha-carboline rearrangements, and Negishi coupling reactions is described.
TetrahedronA simple method for the direct arylation of indoles
63 Citations2008Kyle J. Eastman, Phil S. Baran
Journal of Medicinal ChemistrySynthesis and Biological Evaluation of (−)- and (+)-Debromoflustramine B and Its Analogues as Selective Butyrylcholinesterase Inhibitors
63 Citations2008E. Rivera-Becerril, Pedro Joseph‐Nathan +2 more
The Journal of Organic ChemistryTotal Synthesis of Isoroquefortine C
59 Citations2001Bruno Schiavi, David J. Richard +1 more
A short and efficient total synthesis of isoroquefortine C, the 3,12-(Z)-isomer of roqueforts C, from L-tryptophan methyl ester hydrochloride and 4(5)-(hydroxy)methylimidazole hydrochlorides is described.
TetrahedronLansai A–D, secondary metabolites from Streptomyces sp. SUC1
54 Citations2008Pittaya Tuntiwachwuttikul, Thongchai Taechowisan +3 more
Streptomyces sp.
Organic & Biomolecular ChemistryA rapid stereocontrolled synthesis of the 3a-hydroxy-pyrrolo[2,3-b]indole skeleton, a building block for 10b-hydroxy-pyrazino[1′,2′:1,5]pyrrolo[2,3-b]indole-1,4-diones
51 Citations2003Steven V. Ley, Ed Cleator +1 more
A two-step selenocyclisation-oxidative deselenaton sequence was used to establish the 3a-hydroxy-pyrrolo[2,3-b]indole core and these tricycles were used as effective precursors to 10b-Hydroxy-pyrazino[1',2':1,5]pyrrole-1,4-diones.
The Journal of Organic ChemistryOn the Reaction of Tryptophan Derivatives with <i>N</i>-Phenylselenyl Phthalimide: The Nature of the Kinetic and Thermodynamic Hexahydropyrrolo[2,3-<i>b</i>]indole Products. Alkylation of Tryptophan with Inversion of Configuration
50 Citations1999David Crich, Xianhai Huang
The Journal of Organic ChemistrySynthesis and Evaluation of CC-1065 and Duocarmycin Analogs Incorporating the 1,2,3,4,11,11a-Hexahydrocyclopropa[<i>c</i>]naphtho[2,1-<i>b</i>]azepin-6-one (CNA) Alkylation Subunit: Structural Features that Govern Reactivity and Reaction Regioselectivity
49 Citations1997Dale L. Boger, Philip Turnbull
Tetrahedron LettersA novel and efficient total synthesis of (±)-physostigmine
31 Citations2009Mukund G. Kulkarni, Attrimuni P. Dhondge +8 more
Journal of the Chemical Society Perkin Transactions 1Sporidesmins. Part 16. The structure of chetomin, a toxic metabolite of Chaetomium cochliodes, by nitrogen-15 and carbon-13 nuclear magnetic resonance spectroscopy
29 Citations1978Dyanne Brewer, A. G. McInnes +5 more
Organic LettersBidirectional Synthesis of the Central Amino Acid of Chloptosin
28 Citations2006Wen‐Xu Hong, Ling-Jun Chen +2 more
MacromoleculesSynthesis and Polymerization Studies of Bicyclo[2.1.0]pentane-1-carbonitrile and Bicyclo[3.1.0]hexane-1-carbonitrile
18 Citations1971H. K. Hall
HeterocyclesSynthesis of Optically Active Methyl 1,2,3,3a,8,8a-Hexahydropyrrolo[2,3-b]indole-2-carboxylates Having a Halogen or an Oxygen Functional Group at the 3a-Position
10 Citations2006Masanori Somei, Fumio Yamada +5 more
Bulletin of the Chemical Society of JapanStereoselective Syntheses of (<i>E</i>)-α,β-Didehydroamino Acid and Peptide Containing Its Residue Utilizing Oxazolidinone Derivative
10 Citations2009Miki Kometani, Kohki Ihara +2 more