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Total Synthesis, Relay Synthesis, and Structural Confirmation of the C18-Norditerpenoid Alkaloid Neofinaconitine

https://doi.org/10.1021/ja4064958
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What this work says

Outgoing claims: the papers this work cites, builds on, or argues with.

inferredcites →https://doi.org/10.1002/adsc.200600642openalex-snapshot
Incorporation of Primary Amines into a Polyester Chain by a Combination of Chemical and Lipase‐Catalyzed ε‐Caprolactone Ring‐Opening Processes
inferredcites →https://doi.org/10.1002/anie.200803344openalex-snapshot
Stable 5‐Substituted Cyclopentadienes for the Diels–Alder Cycloaddition and their Application to the Synthesis of Palau'amine
inferredcites →https://doi.org/10.1002/ardp.19062440119openalex-snapshot
Ueber das Akonitin und das Akonin aus Aconitum Napellus
inferredcites →https://doi.org/10.1002/ardp.19222600113openalex-snapshot
Zur Kenntnis des Lappakonitins
inferredcites →https://doi.org/10.1002/jlac.19284600106openalex-snapshot
Synthesen in der hydroaromatischen Reihe
inferredcites →https://doi.org/10.1016/0040-4020(95)01123-4openalex-snapshot
1,2,2-tribromocyclopropanecarboxylic acid and derivatives—Valuable intermediates for four carbon cyclopropane and cyclopropene synthons
inferredcites →https://doi.org/10.1016/0223-5234(92)90195-7openalex-snapshot
The Alkaloids, Chemistry and Pharmacology
inferredcites →https://doi.org/10.1016/j.tet.2004.05.024openalex-snapshot
Synthesis of simple analogues of methyllycaconitine—an efficient method for the preparation of the N-substituted anthranilate pharmacophore
inferredcites →https://doi.org/10.1016/j.tet.2011.04.062openalex-snapshot
Construction of AE ring system for the C19-diterpenoid alkaloids with a 5β-hydroxyl group
inferredcites →https://doi.org/10.1016/s0031-9422(00)86890-9openalex-snapshot
Cardioactive steroid saponins and other constituents from the aerial parts of tribulus cistoides☆
inferredcites →https://doi.org/10.1016/s0031-9422(00)89756-3openalex-snapshot
Diterpenoid alkaloids from ayurvedic processed and unprocessed Aconitum ferox
inferredcites →https://doi.org/10.1016/s0031-9422(98)00547-0openalex-snapshot
Diterpenoid alkaloids from Delphinium crispulum
inferredcites →https://doi.org/10.1016/s0040-4020(01)86466-8openalex-snapshot
1-Oxa-2,3-cyclohexadiene (“2H-isopyran”): A strained heterocyclic allene undergoing cycloaddition reactions with characteristic typo-, regio- and stereoselectivities
inferredcites →https://doi.org/10.1016/s0040-4020(01)92477-9openalex-snapshot
The structures of talatisamine and cammaconine by correlation with isotalatizidine
inferredcites →https://doi.org/10.1016/s0040-4020(01)93887-6openalex-snapshot
Hydrogen migration in cyclopentadienes
inferredcites →https://doi.org/10.1016/s0040-4020(01)96490-7openalex-snapshot
Some highlights in the structural and synthetic chemistry of the aconite alkaloids
inferredcites →https://doi.org/10.1016/s0040-4020(96)01169-6openalex-snapshot
The preparation of optically active 2-cyclopenten-1,4-diol derivatives from furfuryl alcohol
inferredcites →https://doi.org/10.1016/s0040-4039(00)84207-0openalex-snapshot
An efficient and highly regioselective intramolecular Mannich-type reaction: A construction of the AEF ring system of aconitine-type diterpene alkaloids
inferredcites →https://doi.org/10.1016/s0040-4039(01)82712-xopenalex-snapshot
The structure of aconitine
inferredcites →https://doi.org/10.1016/s0040-4039(01)91316-4openalex-snapshot
N-methoxy-n-methylamides as effective acylating agents
inferredcites →https://doi.org/10.1016/s0040-4039(01)99415-8openalex-snapshot
The structure of delphinine
inferredcites →https://doi.org/10.1016/s0301-0082(98)00037-9openalex-snapshot
The effects of Aconitum alkaloids on the central nervous system
inferredcites →https://doi.org/10.1016/s1099-4831(08)00210-1openalex-snapshot
The Alkaloids Chemistry and Biology
inferredcites →https://doi.org/10.1016/s1099-4831(09)06701-7openalex-snapshot
Chapter 1 The C18-Diterpenoid Alkaloids
inferredcites →https://doi.org/10.1016/s1099-4831(09)06708-xopenalex-snapshot
The alkaloids Chemistry and Biology
inferredcites →https://doi.org/10.1016/s1099-4831(10)69001-3openalex-snapshot
The C19-Diterpenoid Alkaloids
inferredcites →https://doi.org/10.1021/ja00165a038openalex-snapshot
Total syntheses of (+)- and (-)-didemnenones A and B. Anti selectivity in the intramolecular carbomercuration reaction
inferredcites →https://doi.org/10.1021/ja00240a036openalex-snapshot
Hydrolysis of an amide in a carboxypeptidase model using cobalt(III) and bifunctional catalysts
inferredcites →https://doi.org/10.1021/ja00822a048openalex-snapshot
Total synthesis of talatisamine, a delphinine type alkaloid
inferredcites →https://doi.org/10.1021/ja00997a067openalex-snapshot
Sulfur trioxide in the oxidation of alcohols by dimethyl sulfoxide
inferredcites →https://doi.org/10.1021/ja01468a042openalex-snapshot
The Utility of Phosphonate Carbanions in Olefin Synthesis
inferredcites →https://doi.org/10.1021/ja01509a045openalex-snapshot
Cyclopropene. V. Some Reactions of Cyclopropene1
inferredcites →https://doi.org/10.1021/jo00115a015openalex-snapshot
Titanium and Boron Mediated Aldol Reactions of .beta.-Hydroxy Ketones
inferredcites →https://doi.org/10.1021/jo00397a015openalex-snapshot
Crown-cation complex effects. 8. Reactions of crown ether activated tert-butoxide ion
inferredcites →https://doi.org/10.1021/jo00915a036openalex-snapshot
Organoselenium chemistry. .alpha.-Phenylseleno lactones. New general route to the synthesis of fused .alpha.-methylene lactones
inferredcites →https://doi.org/10.1021/jo051155yopenalex-snapshot
A Model Study toward the Total Synthesis of N-Deacetyllappaconitine
inferredcites →https://doi.org/10.1021/jo961710jopenalex-snapshot
Facial Selectivity in the Diels−Alder Reactions of 5-Chloro-, 5-Bromo-, and 5-Iodo-1,3-cyclopentadiene and Derivatives
inferredcites →https://doi.org/10.1021/jo9707949openalex-snapshot
Diels−Alder Reactions of 5-Alkyl-1,3-cyclopentadienes
inferredcites →https://doi.org/10.1021/ol006982uopenalex-snapshot
A Concise Enantioselective Synthesis of a Key A-Ring Synthon for 1α-Hydroxyvitamin D3 Compounds
inferredcites →https://doi.org/10.1021/ol035542aopenalex-snapshot
Useful Enantioselective Bicyclization Reactions Using an N-Protonated Chiral Oxazaborolidine as Catalyst
inferredcites →https://doi.org/10.1021/ol100290aopenalex-snapshot
An Expedient Procedure for the Oxidative Cleavage of Olefinic Bonds with PhI(OAc)2, NMO, and Catalytic OsO4
inferredcites →https://doi.org/10.1021/ol702375ropenalex-snapshot
C−H Amination in Synthesis: An Approach to the Assembly of the B/C/D Ring System of Aconitine
inferredcites →https://doi.org/10.1039/b916679copenalex-snapshot
Diterpenoid alkaloids
inferredcites →https://doi.org/10.1039/c39800000739openalex-snapshot
Exclusive syn-addition in Diels–Alder additions to a 1-hydroxycyclopenta-2,4-diene
inferredcites →https://doi.org/10.1039/p19810002684openalex-snapshot
Some photochemical and oxidative conversions of pterocarpans and isoflavans: functional requirements for cyclization of isoflavans to pterocarpans
inferredcites →https://doi.org/10.1039/p19920001891openalex-snapshot
5-Fluorocyclopentadiene: synthesis and utility
inferredcites →https://doi.org/10.1071/ch9752175openalex-snapshot
Substituted endo -Tricyclo[3,2,1,02,4]oct-6-enes. I. Preparation by the Diels-Alder reaction between cyclopropene and substituted cyclopentadienes
inferredcites →https://doi.org/10.1080/00397918208061938openalex-snapshot
An Alternative Procedure for the Aluminum-Mediated Conversion of Esters to Amides
inferredcites →https://doi.org/10.1139/v06-144openalex-snapshot
Some oxidation products of lycoctonine revisited
inferredcites →https://doi.org/10.1139/v76-149openalex-snapshot
The synthesis of chasmanine: aromatic intermediate
inferredcites →https://doi.org/10.1139/v78-237openalex-snapshot
A new stereospecific total synthesis of chasmanine and 13-desoxydelphonine
inferredcites →https://doi.org/10.1351/pac197951040689openalex-snapshot
Total synthesis of delphinine-type alkaloids by simple, fourth generation methods
inferredcites →https://doi.org/10.3987/s-1977-01-0217openalex-snapshot
A Stereospecific Total Synthesis of Chasmanine

What points at this work

Incoming claims: where this work appears in other papers’ reference lists and arguments.

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Diterpenoid alkaloids from the whole herb of Delphinium grandiflorum L
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Palladium‐Catalyzed Two‐Component Domino Coupling Reaction of (Z)‐β‐Bromostyrenes with Norbornenes: Synthesis of 1,5‐Enynes
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Enantioselective Carbene Cascade: An Effective Approach to Cyclopentadienes and Applications in Diels–Alder Reactions
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Gold‐Catalyzed Cycloisomerizations of Functionalyzed Cyclopropyl Alkynes: the Cases of Carboxamides and Alcohols
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Ongoing Pursuit of Diterpenoid Alkaloids: A Synthetic View
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Synthese des C18‐Norditerpenoid‐Alkaloids Neofinaconitin: eine Lektion in konvergenter Syntheseplanung
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Synthesis of Atisine, Ajaconine, Denudatine, and Hetidine Diterpenoid Alkaloids by a Bioinspired Approach
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Stereoselective Total Synthesis of Hetisine‐type C20‐Diterpenoid Alkaloids: Spirasine IV and XI
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Total Synthesis of Talatisamine
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Synthesis of the C18‐Norditerpenoid Alkaloid Neofinaconitine: A Lesson in Convergent Synthesis Planning
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Synthesis of Atisine, Ajaconine, Denudatine, and Hetidine Diterpenoid Alkaloids by a Bioinspired Approach
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Stereoselective Total Synthesis of Hetisine‐type C20‐Diterpenoid Alkaloids: Spirasine IV and XI
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Total Synthesis of Talatisamine
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Expedient Construction of the Hexacycle of Franchetine
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Synthesis of Nature‐Inspired Medium‐Sized Fused Heterocycles from Amino Acids
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Collective Synthesis of Schilancidilactones A, B and Schilancitrilactones A, B, C, 20‐epi‐Schilancitrilactone A
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Total Syntheses of Highly Oxidized Natural Products†
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Radical Reactions in Alkaloid Synthesis: A Perspective from Carbon Radical Precursors
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Bonding and Diels–Alder reactions of substituted 2-borabicyclo(1.1.0)but-1(3)-enes: a theoretical study
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The diterpenoid alkaloids
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Rapid construction of the unique BCD ring system of tricyclo[6.2.1.0]undecane in the C 19 -diterpenoid alkaloid aconitine
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Assembly of the 6/3/5/6 tetracyclic core of rearranged-type C19-diterpenoid alkaloids
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Computational study on the mechanism of uncatalyzed and selenium-based catalyzed bromolactonization
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Theoretical predication of Diels-Alder reactions of highly strained dienophiles
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Two new entries to the ABF tricyclic ring system of 7,17-seco-type C19-diterpenoid alkaloids via free radical cyclization and [3+2] cycloaddition of nitrile oxide
inferred← citeshttps://doi.org/10.1016/j.tet.2020.131385openalex-snapshot
Construction of the ABCE-ring structure of talatisamine via decarboxylative radical cyclization
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Solid-phase synthesis of fused 1,4-diazepanone peptidomimetics via tandem N-iminium ion cyclization–nucleophilic addition
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A new route to BCD tricyclic fragment of C19-diterpenoid alkaloids via intramolecular Pauson-Khand reaction followed by anionic 1,2-migration rearrangement
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Enantioselective route to an AE-ring intermediate in the total synthesis of talatisamine
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Synthesis of Three-Dimensionally Fascinating Diterpenoid Alkaloids and Related Diterpenes
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Click Chemistry with Cyclopentadiene
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Cutting-Edge and Time-Honored Strategies for Stereoselective Construction of C–N Bonds in Total Synthesis
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Cyclopropanation Strategies in Recent Total Syntheses
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High-Pressure-Promoted and Facially Selective Diels–Alder Reactions of Enzymatically Derived cis-1,2-Dihydrocatechols and Their Acetonide Derivatives: Enantiodivergent Routes to Homochiral and Polyfunctionalized Bicyclo[2.2.2]octenes
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Asymmetric Synthesis of the Functionalized A/E-Ring Fragment of C18-Diterpenoid Alkaloids
inferred← citeshttps://doi.org/10.1021/acs.joc.5b00174openalex-snapshot
Theoretical Analysis of Reactivity Patterns in Diels–Alder Reactions of Cyclopentadiene, Cyclohexadiene, and Cycloheptadiene with Symmetrical and Unsymmetrical Dienophiles
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Construction of the Fused Pentacycle of Talatisamine via a Combination of Radical and Cationic Cyclizations
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Hyperconjugative Aromaticity and Antiaromaticity Control the Reactivities and π-Facial Stereoselectivities of 5-Substituted Cyclopentadiene Diels–Alder Cycloadditions
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Cu(I)-Catalyzed Oxidative Cyclization of Enynamides: Regioselective Access to Cyclopentadiene Frameworks and 2-Aminofurans
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Cyclopentadiene Construction via Rh-Catalyzed Carbene/Alkyne Metathesis Terminated with Intramolecular Formal [3 + 2] Cycloaddition
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Polyene Cyclization/Mannich Cascade for Streamlined Construction of the A/E/F Tricyclic System of Diterpenoid Alkaloids
inferred← citeshttps://doi.org/10.1021/acs.orglett.6b00789openalex-snapshot
Total Synthesis of (−)-Cardiopetaline
inferred← citeshttps://doi.org/10.1021/acs.orglett.6c00571openalex-snapshot
Total Synthesis of Acorane-Type Sesquiterpenes (±)-Bilaiaeacorenol B and (±)-Penicibilaenes A and B
inferred← citeshttps://doi.org/10.1021/acs.orglett.6c02795openalex-snapshot
Construction of a Chasmanine Skeleton Enabled by Hg(OAc)2-Promoted Vinylogous Mannich Reaction
inferred← citeshttps://doi.org/10.1021/acs.orglett.7b02812openalex-snapshot
Synthesis of Cardiopetaline via a Wagner–Meerwein Rearrangement without Preactivation of the Pivotal Hydroxy Group
inferred← citeshttps://doi.org/10.1021/acscentsci.1c00540openalex-snapshot
Total Syntheses of the C 19 Diterpenoid Alkaloids (−)-Talatisamine, (−)-Liljestrandisine, and (−)-Liljestrandinine by a Fragment Coupling Approach
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Convergent Strategies in Total Syntheses of Complex Terpenoids
inferred← citeshttps://doi.org/10.1021/ja503023hopenalex-snapshot
Total Synthesis of (−)-Lepenine
inferred← citeshttps://doi.org/10.1021/jacs.1c01865openalex-snapshot
Asymmetric Total Synthesis of Hetidine-Type C 20 -Diterpenoid Alkaloids: (+)-Talassimidine and (+)-Talassamine
inferred← citeshttps://doi.org/10.1021/jacs.2c11259openalex-snapshot
Total Synthesis of Puberuline C
inferred← citeshttps://doi.org/10.1021/jacs.3c00318openalex-snapshot
Total Synthesis of Vilmoraconitine
inferred← citeshttps://doi.org/10.1021/jacs.3c10362openalex-snapshot
Asymmetric Synthesis of Cyclopamine, a Hedgehog (Hh) Signaling Pathway Inhibitor
inferred← citeshttps://doi.org/10.1021/jacs.5c14513openalex-snapshot
Total Syntheses of Giraldine I and Heterophyllisine
inferred← citeshttps://doi.org/10.1021/jacs.5c19459openalex-snapshot
Asymmetric Total Synthesis of Vilmotenitine A and Structural Revision of Hemsleyaconitine F
inferred← citeshttps://doi.org/10.1021/jacs.6b10463openalex-snapshot
Hyperconjugative, Secondary Orbital, Electrostatic, and Steric Effects on the Reactivities and Endo and Exo Stereoselectivities of Cyclopropene Diels–Alder Reactions
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Total Synthesis of the Caged Indole Alkaloid Arboridinine Enabled by aza-Prins and Metal-Mediated Cyclizations
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Studies on C20-Diterpenoid Alkaloids: Synthesis of the Hetidine Framework and Its Application to the Synthesis of Dihydronavirine and the Atisine Skeleton
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From Amino Acids to Nature-Inspired Molecular Scaffolds: Incorporation of Medium-Sized Bridged Heterocycles into a Peptide Backbone
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Expedient Construction of the ABEF Azatetracyclic Ring Systems of Lycoctonine-Type and 7,17-seco-Type C19-Diterpenoid Alkaloids
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Palladium(0)-Catalyzed Methylenecyclopropanation of Norbornenes with Vinyl Bromides
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A three-component coupling approach to the ACE-ring substructure of C19-diterpene alkaloids
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Network-analysis-guided synthesis of weisaconitine D and liljestrandinine
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Total synthesis of atropurpuran
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Palladium(0)-catalyzed cyclopropanation of benzyl bromides via C(sp 3 )–H bond activation
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Fluorescent natural products as probes and tracers in biology
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Expeditious synthesis of the fused hexacycle of puberuline C via a radical-based cyclization/translocation/cyclization process
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Effect of protic additives in Cu-catalysed asymmetric Diels–Alder cycloadditions of doubly activated dienophiles: towards the synthesis of magellanine-type Lycopodium alkaloids
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Enabling syntheses of diterpenoid alkaloids and related diterpenes by an oxidative dearomatization/Diels–Alder cycloaddition strategy
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Recent advances in the intramolecular Mannich reaction in natural products total synthesis
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Construction of the highly oxidized bicyclo[3.2.1]octane CD ring system of aconitine via a late stage enyne cycloisomerization
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Total synthesis of C 19 -diterpenoid alkaloid: construction of a functionalized ABCDE-ring system
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Progress towards the synthesis of aconitine: construction of the AE fragment and attempts to access the pentacyclic core
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An invocation for computational evaluation of isomerization transforms: cationic skeletal reorganizations as a case study
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Synthesis of tricyclo[7.2.1.0 9,10 ]dodecan-11-one core ring systems of norditerpenoid alkaloids and racemulosine
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The 1α-hydroxy-A-rings of norditerpenoid alkaloids are twisted-boat conformers
inferred← citeshttps://doi.org/10.1039/d2qo01740gopenalex-snapshot
Aconitine synthesis studies. A modeling construction of the functionalized BCDE tetracyclic ring system
inferred← citeshttps://doi.org/10.1039/d3ob00647fopenalex-snapshot
Construction of the tetracyclic ring system of diterpene alkaloids via cationic [5 + 2] cycloaddition
inferred← citeshttps://doi.org/10.1039/d4ob00561aopenalex-snapshot
Stereocontrolled synthesis of the aconitine D ring from d -glucose
inferred← citeshttps://doi.org/10.1039/d4ra02821jopenalex-snapshot
A concise and stereoselective synthesis of the BCDF tetracyclic ring system of C 19 -diterpenoid alkaloids
inferred← citeshttps://doi.org/10.1039/d4sc05890aopenalex-snapshot
Oxidative generation of isobenzofurans from phthalans: application to the formal synthesis of (±)-morphine
inferred← citeshttps://doi.org/10.1039/d5cc02783gopenalex-snapshot
Synthesis of cyclopropanes via palladium-catalyzed [2+1] annulations of sulfoxonium ylides and norbornenes
inferred← citeshttps://doi.org/10.1039/d6qo00212aopenalex-snapshot
An expedient modeling construction of a BCDEF pentacyclic ring system analog of aconitine and racemulosine
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Synthesis of Polycyclic Frameworks through Iron-Catalyzed Intramolecular [5+2] Cycloaddition
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Recent Advances Towards Syntheses of Diterpenoid Alkaloids
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Synthesis of Polycyclic Natural Products through Skeletal Rearrangement
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The Future of Retrosynthesis and Synthetic Planning: Algorithmic, Humanistic or the Interplay?
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Nature-inspired catalytic asymmetric rearrangement of cyclopropylcarbinyl cation
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Total Synthesis of Talatisamine: Exploration of Convergent Synthetic Strategies
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Recent Advances in the Chemistry of Saturated Annulated Nitrogen-Containing Polycyclic Compounds
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Recent Progress in the Total Synthesis of Diterpenoid Alkaloids
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