[3,3]-Sigmatropic rearrangements: recent applications in the total synthesis of natural products

scientific article published on 02 September 2009

[3,3]-Sigmatropic rearrangements: recent applications in the total synthesis of natural products is …
instance of (P31):
scholarly articleQ13442814
review articleQ7318358

External links are
P356DOI10.1039/B901177N
P932PMC publication ID4103198
P698PubMed publication ID19847347

P2093author name stringArmen Zakarian
Craig E Stivala
Elizabeth A Ilardi
P2860cites workTotal synthesis of (+/-)-actinophyllic acidQ24642045
An Enantiospecific Synthesis of the Potent Immunosuppressant FR901483 Dr. G. Scheffler and H. Seike contributed equally to this work. We thank Dr. L. B. Pasternack and Dr. D. H. Huang for NMR spectroscopic assistance, and Dr. G. Siuzdak for mass speQ30627164
Synthesis of azadirachtin: a long but successful journeyQ34005420
Synthetic studies on perophoramidine and the communesins: construction of the vicinal quaternary stereocentersQ37179632
Biomimetic total synthesis of gambogin and rate acceleration of pericyclic reactions in aqueous media.Q40469335
Strain-release rearrangement of N-vinyl-2-arylaziridines. Total synthesis of the anti-leukemia alkaloid (-)-deoxyharringtonineQ41940516
Explorations in organic chemistry leading to the total synthesis of (+/-)-gelsemineQ44099765
Total synthesis of (+/-)-didehydrostemofoline (asparagamine A) and (+/-)-isodidehydrostemofolineQ44259107
Highly efficient transfer of chirality from macrocyclic conformation in the tandem oxy-Cope/Claisen/ene reactionQ44967001
A formal total synthesis of (-)-FR901483, using a tandem cationic aza-Cope rearrangement/Mannich cyclization approachQ45241467
Direct synthesis of (+)-erogorgiaene through a kinetic enantiodifferentiating stepQ45265914
Total synthesis of glycocinnasperimicin D.Q46544634
Total synthesis of solandelactones A, B, E, and F exploiting a tandem Petasis-Claisen lactonization strategyQ46615063
Stereocontrolled synthesis of polyfunctionalized cis-decalins from 2-methoxyphenols: total syntheses of (+/-)-eremopetasidione, (+/-)-3 beta-angeloyloxyfuranoeremophilane, and (+/-)-3 beta-methacryloyloxyfuranoeremophilaneQ46715277
Combined C-H activation/cope rearrangement as a strategic reaction in organic synthesis: total synthesis of (-)-colombiasin a and (-)-elisapterosin B.Q46944383
A relay route for the synthesis of azadirachtin.Q52681920
An Enantioselective Total Synthesis of (+)- and (−)-Saudin. Determination of the Absolute ConfigurationQ60455457
Total synthesis of (+)-arteanniun M using the tandem oxy-Cope/ene reactionQ74018743
Stereocontrolled total synthesis of alkaloid G via the oxy-anion Cope rearrangement and improved total synthesis of (+)-ajmalineQ74103231
The first total synthesis of (+/-)-eremopetasidioneQ74110198
Total Synthesis of 1‐O‐MethyllaterifloroneQ79075938
Formal total synthesis of (+)-zaragozic acid C through an Ireland-Claisen rearrangementQ80188351
Studies toward the total synthesis of Wiedemannic acidQ80540627
Acyclic stereocontrol in the Ireland-Claisen rearrangement of alpha-branched estersQ80786879
Total synthesis of (+)-pinnatoxin AQ80801285
Total synthesis of (+/-)-frondosin BQ80830800
Total synthesis of (+/-)-communesin FQ81486749
Total synthesis of (+/-)--trichodermamide B and of a putative biosynthetic precursor to aspergillazine a using an oxaza-cope rearrangementQ81693135
Development of the 1,2-oxaza-Cope rearrangementQ83166086
"Biomimetic" Cascade Reactions in Organic Synthesis: Construction of 4-Oxatricyclo[4.3.1.0]decan-2-one Systems and Total Synthesis of 1-O-Methylforbesione via Tandem Claisen Rearrangement/Diels-Alder ReactionsQ88522243
P433issue11
P921main subjectnatural productQ901227
P304page(s)3133-3148
P577publication date2009-09-02
P1433published inChemical Society ReviewsQ2962268
P1476title[3,3]-Sigmatropic rearrangements: recent applications in the total synthesis of natural products
P478volume38

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cites work (P2860)
Q89089527A Nitrone Dipolar Cycloaddition Strategy toward an Enantioselective Synthesis of Massadine
Q41675613A Short Synthesis of Aphanamol I in Both Racemic and Enantiopure Forms
Q37707982A computational triage approach to the synthesis of novel difluorocyclopentenes and fluorinated cycloheptadienes using thermal rearrangements
Q49062359A core switching strategy to pyrrolo[2,3-b]quinolines and diazocino[1,2-a]indolinones.
Q51757875A synthetic approach for constructing the 3/6/6/5-fused tetracyclic skeleton of tenuipesine A.
Q53729430An Asymmetric Redox Arylation: Chirality Transfer from Sulfur to Carbon through a Sulfonium [3,3]-Sigmatropic Rearrangement.
Q48136720An Enyne Cope Rearrangement Enables Polycycloalkane Synthesis from Readily Available Starting Materials.
Q40477313An unexpected rearrangement of pyrazolium halides based on N-N bond cleavage: synthesis of 1,2-dihydropyrimidines.
Q89839837Asymmetric Total Syntheses of Di- and Sesquiterpenoids by Catalytic C-C Activation of Cyclopentanones
Q48109615Asymmetric Total Synthesis of (-)-Erogorgiaene and Its C-11 Epimer and Investigation of Their Antimycobacterial Activity
Q44451133Cascade- and orthoamide-type Overman rearrangements of allylic vicinal diols
Q36452957Catalytic asymmetric Claisen rearrangement of enolphosphonates: construction of vicinal tertiary and all-carbon quaternary centers
Q41986037Construction of vicinal tertiary and all-carbon quaternary stereocenters via Ir-catalyzed regio-, diastereo-, and enantioselective allylic alkylation and applications in sequential Pd catalysis
Q89115328Copper-catalyzed [1,2]-rearrangements of allylic iodides and aryl α-diazoacetates
Q38579612Direct construction of vicinal all-carbon quaternary stereocenters in natural product synthesis
Q53642449Enantioselective Total Synthesis of (+)-Neostenine.
Q50218565Enantioselective construction of branched 1,3-dienyl substituted quaternary carbon stereocenters by asymmetric allenyl Claisen rearrangement
Q34019870Enantioselective synthesis of tatanans A-C and reinvestigation of their glucokinase-activating properties
Q57250343Evidence for a Sigmatropic and an Ionic Pathway in the Winstein Rearrangement
Q46766801Fusing cubanes to 1,5-hexadiene
Q48294710Indium triflate catalysed 3-aza-Cope rearrangement of amino acid derived α,β-unsaturated esters to alkylidene oxindoles
Q45961249Iridium-Catalyzed Stereoselective Allylic Alkylation Reactions with Crotyl Chloride.
Q52935544Ligand-Controlled Regiodivergence in the Copper-Catalyzed [2,3]- and [1,2]-Rearrangements of Iodonium Ylides.
Q38745582Navigating the Chiral Pool in the Total Synthesis of Complex Terpene Natural Products.
Q50449707Nickel(II)-catalyzed asymmetric propargyl and allyl Claisen rearrangements to allenyl- and allyl-substituted β-ketoesters
Q33574701Palladium-Catalyzed Enantioselective Heck Alkenylation of Trisubstituted Allylic Alkenols: A Redox-Relay Strategy to Construct Vicinal Stereocenters
Q40778951Pericyclic cascade with chirality transfer: reaction pathway and origin of enantioselectivity of the hetero-Claisen approach to oxindoles
Q46756670Re-examining the mechanisms of competing pericyclic reactions of 1,3,7-octatriene
Q47253440Recent Advances in Enzymatic Complexity Generation: Cyclization Reactions
Q39168195Recent advances in the Overman rearrangement: synthesis of natural products and valuable compounds.
Q64923674Recent developments in the Reformatsky-Claisen rearrangement.
Q46131677SAM-dependent enzyme-catalysed pericyclic reactions in natural product biosynthesis
Q46862564Stereodefined acyclic trisubstituted metal enolates towards the asymmetric formation of quaternary carbon stereocentres
Q55001857Stereodivergent synthesis of vicinal quaternary-quaternary stereocenters and bioactive hyperolactones.
Q38952662Stereoselective total synthesis and structural elucidation of (-)-indoxamycins A-F.
Q52358248Structural basis of the Cope rearrangement and cyclization in hapalindole biogenesis.
Q50231171Synergistic Kinetic Resolution and Asymmetric Propargyl Claisen Rearrangement for the Synthesis of Chiral Allenes
Q50903078The Ireland-Claisen rearrangement strategy towards the synthesis of the schizophrenia drug, (+)-asenapine.
Q57471976The expanding world of biosynthetic pericyclases: cooperation of experiment and theory for discovery
Q51748765Total synthesis of the antibiotic kendomycin: a macrocyclization using the Tsuji-Trost etherification.
Q42713103α-Amination of keto-nitrones via multihetero-Cope rearrangement employing an imidoyl chloride reagent

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