Enantiospecific, Stereospecific Total Synthesis of the Oxindole Alkaloid Alstonisine
Organic LettersPublished 29 October 2002
Xiangyu Z. Wearing, James M. Cook
Citations68
SJR quartileQ1
SJR score1.24
SNIP1.03
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.
TL;DR
The total synthesis of alstonisine was accomplished in enantiospecific fashion in an overall yield of 12% (from tryptophan methyl ester) in 17 reaction vessels.
Abstract
[reaction: see text] The total synthesis of alstonisine was accomplished in enantiospecific fashion in an overall yield of 12% (from tryptophan methyl ester) in 17 reaction vessels. The structure of alstonisine (1) has been determined by NOE spectroscopic experiments and was confirmed by single-crystal X-ray analysis.
Keywords
ChemistryPharmacology, Toxicology and Pharmaceutics
The Journal of Organic ChemistryIntramolecular alkene arylations for rapid assembly of polycyclic systems containing quaternary centers. A new synthesis of spirooxindoles and other fused and bridged ring systems
326 Citations1987Matthew M. Abelman, Taeboem Oh +1 more
Journal of the American Chemical SocietyN-Phenylselenophthalimide (N-PSP) and N-phenylselenosuccinimide (N-PSS). Two versatile carriers of the phenylseleno group. Oxyselenation of olefins and a selenium-based macrolide synthesis
230 Citations1979K. C. Nicolaou, David A. Claremon +2 more
The Journal of Organic ChemistryCatalytic asymmetric synthesis of quarternary carbon centers. Palladium-catalyzed formation of either enantiomer of spirooxindoles and related spirocyclics using a single enantiomer of a chiral diphosphine ligand
204 Citations1992Atsuyuki Ashimori, Larry E. Overman
PhytochemistryAlkaloids of Alstonia angustifolia
104 Citations1988Kamel Ghédira, Monique Zèches-Hanrot +5 more
Among the 11 novel alkaloids isolated from the leaves and from the stem bark of Alstonia angustifolia from Malaysia, three were monomers: 19,20-dehydro- O -acetyl yohimbine and hydroxystrictamine, and eight were dimers.
Phytotherapy Research<i>In vitro</i> antiamoebic and antiplasmodial activities of alkaloids isolated from <i>Alstonia angustifolia</i> roots
99 Citations1992Colin W. Wright, David J. Allen +5 more
Three dimeric alkaloids, macrocarpamine, macralstonine acetate (semisynthetic) and villastonine were found to possess significant activity against both protozoans, but were 4–8 times less potent than emetine against E. histolytica and 15–50 times more potent than chloroquine against P. falciparum.
Journal of the American Chemical SocietyA high-potential ferrous complex and its conversion to an alkylperoxoiron(III) intermediate. A lipoxygenase model
98 Citations1993Yan Zang, Timothy E. Elgren +2 more
PhytochemistryAlkaloids of Alstonia Muelleriana
97 Citations1972Robert C. Elderfield, Robert E. Gilman
Four indole alkaloids have been isolated and characterized from the tree bark of Alstonia muelleriana Domin and one of these is the previously known dimeric indoles alkaloid, villalstonine.
Tetrahedron LettersSynthesis studies directed toward gelsemine. Preparation of an advanced pentacyclic intermediate
95 Citations1988William G. Earley, Taeboem Oh +1 more
Journal of the American Chemical SocietyBiomimetic transformations among monomeric macroline-related indole alkaloids
87 Citations1978Robert L. Garnick, Philip W. Le Quesne
Tetrahedron LettersControlling stereoselection in intramolecular heck reactions by tailoring the palladium catalyst
86 Citations1992Andrew Madin, Larry E. Overman
The Journal of Organic ChemistryEnantiospecific Total Synthesis of the Sarpagine Related Indole Alkaloids Talpinine and Talcarpine as Well as the Improved Total Synthesis of Alstonerine and Anhydromacrosalhine-methine via the Asymmetric Pictet−Spengler Reaction
81 Citations2000Yu Peng, Tao Wang +2 more
A convenient synthetic route for the enantiospecific, stereospecific preparation of the key intermediate (-)-N(a)-H, N(b)-benzyl tetracyclic ketone 15a via the asymmetric Pictet-Spengler reaction on a multihundred-gram scale has been developed.
Tetrahedron LettersSpirocycles via palladium catalysed cascade cyclisation-carbonylation-anion capture processes.
79 Citations1993Ronald Grigg, Visuvanathar Sridharan
The rate accelerating effect of thallium(I) acetate enables a palladium catalysed cascade cyclisation-carbonylation-anion capture process to occur under mild conditions and leads to spirocyclic ketones, lactones and lactams.
PhytochemistryOxindole alkaloids from Alstonia macrophylla
74 Citations1996Wah-Hun Wong, Pek-Boon Lim +1 more
Two new oxindole alkaloids are isolated from the bark of Alstonia macrophylla and Nb-demethylalstophyllal oxindoles and alstonal are assigned by spectral methods.
Tetrahedron LettersChiral induction in aryl radical cyclisations
67 Citations1989Keith Jones, Clive McCarthy
Journal of the American Chemical SocietyEnantiospecific total synthesis of the ajmaline related alkaloids (-)-suaveoline, (-)-raumacline, and (-)-Nb-methylraumacline
59 Citations1992Xiaoyong Fu, James M. Cook
Journal of the American Chemical Society<b>Interpretation of the Patterson Function of Crystals Containing a Known Molecular Fragment. the Structure of an <b><i>Alstonia</i></b> Alkaloid</b>
58 Citations1963C. E. Nordman, Kazumi Nakatsu
The Journal of Organic ChemistryGeneral approach for the synthesis of ajmaline-related alkaloids. Enantiospecific total synthesis of (-)-suaveoline, (-)-raumacline, and (-)-Nb-methylraumacline
55 Citations1993Xiaoyong Fu, James M. Cook
Journal of the Chemical Society Chemical CommunicationsA total synthesis of gelsemine: oxindole spiroannelation
52 Citations1994Jonathan K. Dutton, Robert W. Steel +3 more
Journal of the Chemical Society Chemical CommunicationsAn efficient synthesis of spiro[cyclohexane-1,3′-indol-2′(3′H)-ones]via radical cyclisation
52 Citations1986Keith Jones, Mervyn Thompson +1 more
Tetrahedron LettersIntramolecular addition of aryl radicals to vinylogous urethanes: studies toward preparation of the oxindole portion of gelsemine
48 Citations1991David J. Hart, Shung Wu
The Journal of Organic ChemistryNucleophilic-type radical cyclizations of indoles: conversion of 2-cyano 3-substituted indoles to spiro-annelated indolines and tetrahydrocarbazolones
48 Citations1993Chau Chen Yang, Han Ting Chang +1 more
Journal of the American Chemical SocietyGeneral approach to the synthesis of macroline-related alkaloids. Stereospecific total synthesis of (-)-alstonerine
47 Citations1990L. H. Zhang, James M. Cook
The Journal of Organic ChemistryEnantiospecific Total Synthesis of the Sarpagine Related Indole Alkaloids Talpinine and Talcarpine: The Oxyanion−Cope Approach
42 Citations1998Yu Peng, James M. Cook
Helvetica Chimica ActaSynthesis of <i>Aristotelia</i>‐Type Alkaloids. Part XII. Total synthesis of (−)‐tasmanine. Stereoelectronic factors that control the rearrangement of 3<i>H</i>‐indol‐3‐ol derivatives to oxindoles ( = 1,3‐dihydro‐2<i>H</i>‐indol‐2‐ones) or to pseudoindoxyls ( =1,2‐dihydro‐3<i>H</i>‐indol‐3‐ones)
41 Citations1993Rolf Güller, Hans‐Jürg Borschberg
Tetrahedron LettersA formal total synthesis of geneserine
39 Citations1987Colin Wright, Madeline Shulkind +2 more
Journal of the Chemical Society Chemical CommunicationsAryl radical cyclisations involving an amide group in the linking chain
38 Citations1992Keith Jones, John M. D. Storey
Cyclisation of 7, 8 and 9via their derived aryl radicals gives products arising from addition of the aryL radical to the acryloyl double bond exclusively.
Helvetica Chimica ActaMacrocarpamin, ein neues Bisindolalkaloid aus <i>Alstonia macrophylla</i> W<scp>ALL</scp>. 167. Mittelung über organische Naturstoffe
38 Citations1978Friedrich Mayerl, Manfred Hesse
Journal of the American Chemical SocietyBiomimetic synthesis of macroline
37 Citations1980Robert W. Esmond, Philip W. Le Quesne
TetrahedronNovel Macroline Oxindoles from a Malayan Alstonia
36 Citations2000Toh‐Seok Kam, Yeun‐Mun Choo
The Journal of Organic ChemistryStudies Directed toward the Enantiospecific Synthesis of Gardneria, Voacanga, and Alstonia Oxindole Alkaloids
32 Citations1995Andrew C. Peterson, James M. Cook
Tetrahedron AsymmetrySynthesis of aristotelia-type alkaloids. Part X. Biomimetic transformation of synthetic (+)-aristoteline into (−)-alloaristoteline.
30 Citations1992Rolf Güller, Hans‐Jürg Borschberg
Tetrahedron LettersDiastereospecific synthesis of ketooxindoles. Potential intermediates for the synthesis of alstonisine as well as for Voachalotine related oxindole alkaloids
30 Citations1997Yu Peng, James M. Cook
Journal of the Chemical Society Perkin Transactions 1Gardneria alkaloids. Part 13. Structure of gardmultine and demethoxygardmultine; bis-type indole alkaloids of Gardneria multiflora Makino
29 Citations1982Shin‐ichiro Sakai, Norio Aimi +3 more
PhytochemistryNb-demethylalstophylline oxindole an oxindole alkaloid from the leaves of Alstonia macrophylla
28 Citations1987Atta‐ur Rahman, W.S.J. Silva +2 more
Journal of the Chemical Society Chemical CommunicationsCobalt(<scp>II</scp>) Chloride–Grignard reagent: an alternative to tin hydride in aryl radical cyclisations
28 Citations1994Andrew J. Clark, D. I. Davies +2 more
Tetrahedron LettersTwo new stereochemically complementary oxindole synthesis
27 Citations1982Ian Fleming, M. Antonietta Loreto +2 more
Chemical and Pharmaceutical BulletinEffect of gardneria alkaloids on ganglionic transmission in the rabbit and rat superior cervical ganglia in situ.
27 Citations1978Masatoshi Harada, Yukihiro Ozaki
Among these compounds, the most potent ganglion blocking effect was found in gardneramine, gardnerine, and Alkaloid I, and the effect of hydroxygardnutine and 18-demethylgardneramine was very weak.
Tetrahedron LettersSynthetic applications of -Aryl- -acyl hydroxymic acids. A convenient route to 3-substituted -Benzoyl oxindoles
26 Citations1991Paulo Almeida, Sundaresan Prabhakar +2 more
HeterocyclesStudies in the Formation of Oxidoles from Their Indolozabicyclo[3.3.1]nonane Counterparts and Implications for the Biogenesis of Alstonisine
24 Citations1989James M. Cook, Sean P. Hollinshead +2 more
Tetrahedron LettersA stereoselective transformation of pseudoindoxyls into oxindoles in a single operation
21 Citations1994Rolf Güller, Hans‐Jürg Borschberg
YAKUGAKU ZASSHIGardneria Alkaloids. IV. : Comparative Study of Alkaloids on Gardneria nutans SIEB. et ZUCC., G. Multiforia MAKINO, G. Shimadai HAYATA and So-called G. Insularis NAKAI
18 Citations1970Joju Haginiwa, Shin‐ichiro Sakai +3 more
Chemical and Pharmaceutical BulletinStructure of gardneramine and 18-demethylgardneramine.
18 Citations1975Shin‐ichiro Sakai, Norio Aimi +6 more
TetrahedronAn efficient synthetic pathway to the macroline-type indole alkaloids, talcarpine and alstonerine from ajmaline.
16 Citations1991Hiromitsu Takayama, Chada Phisalaphong +3 more
Journal of the American Chemical Society[3,3]-Sigmatropic rearrangements in indoloazabicyclo[3.3.1]nonene systems. Reversal of the stereofacial selectivity in the Claisen vs. the ortho ester Claisen rearrangement
15 Citations1989Lin Hua Zhang, Mark L. Trudell +2 more
Journal of the Chemical Society Perkin Transactions 1X-Ray structure determination of gardmultine. A bis-indole alkaloid isolated from Gardneria multiflora Makino
11 Citations1982J. V. Silverton, Toshiyuki Akiyama
Chemical and Pharmaceutical Bulletin2-Substituted thiazolines. III. Reaction with N-benzoyl-.ALPHA.-amino acids.
8 Citations1975TOSHIYUKI OKUTOME, Y. SAKURAI +4 more
