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Unified Total Syntheses of Fawcettimine Class Alkaloids: Fawcettimine, Fawcettidine, Lycoflexine, and Lycoposerramine B

https://doi.org/10.1021/jo3006045
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What this work says

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

inferredcites →https://doi.org/10.1002/1521-3765(20010803)7:15<3321::aid-chem3321>3.0.co;2-hopenalex-snapshot
Highly Efficient Deacetylation by Use of the Neutral Organotin Catalyst [tBu2SnOH(Cl)]2
inferredcites →https://doi.org/10.1002/anie.200702695openalex-snapshot
Total Synthesis of (+)‐Fawcettimine
inferredcites →https://doi.org/10.1002/anie.200800522openalex-snapshot
Total Synthesis of (+)‐Fawcettidine
inferredcites →https://doi.org/10.1002/anie.201008147openalex-snapshot
Total Synthesis of (±)‐Alopecuridine and Its Biomimetic Transformation into (±)‐Sieboldine A
inferredcites →https://doi.org/10.1002/hlca.200590213openalex-snapshot
Enantioselective Syntheses and Fragrance Properties of the Four Stereoisomers of Magnolione® (Magnolia Ketone)
inferredcites →https://doi.org/10.1007/s10593-008-0042-4openalex-snapshot
The Mitsunobu reaction in the chemistry of nitrogen-containing heterocyclic compounds. The formation of heterocyclic systems (review)
inferredcites →https://doi.org/10.1016/0031-9422(79)80193-4openalex-snapshot
Alkaloids of Lycopodium magellanicum
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The first example of the [4+2] cycloaddition reaction of silylketenes with 1,3-dienes: A convenient preparation of 2-pyranones and isochromenes
inferredcites →https://doi.org/10.1016/j.tet.2011.05.107openalex-snapshot
Ten new fawcettimine-related alkaloids from three species of Lycopodium
inferredcites →https://doi.org/10.1016/s0040-4020(01)01059-6openalex-snapshot
Synthesis of methyl epijasmonate and cis -3-(2-oxopropyl)-2-(pent-2 Z -enyl)-cyclopentan-1-one
inferredcites →https://doi.org/10.1016/s0040-4020(01)96203-9openalex-snapshot
Medium ring nitrogen heterocyles
inferredcites →https://doi.org/10.1016/s0040-4020(02)00664-6openalex-snapshot
CP-263,114 synthetic studies. Construction of an isotwistane ring system via rhodium carbenoid C–H insertion
inferredcites →https://doi.org/10.1016/s0040-4039(00)80137-9openalex-snapshot
A general method for the selective reduction of ketones in the presence of enones.
inferredcites →https://doi.org/10.1016/s0040-4039(00)90638-5openalex-snapshot
Structure of fawcettimine: Correlation with serratinine
inferredcites →https://doi.org/10.1016/s0040-4039(01)86574-6openalex-snapshot
Stereoselective syntheses of lycopodium alkaloids, (±)-fawcettimine and (±)-8-deoxyserratinine
inferredcites →https://doi.org/10.1016/s0040-4039(01)87644-9openalex-snapshot
Lycoflexine, a new type of lycopodium alkaloid
inferredcites →https://doi.org/10.1021/cr990407qopenalex-snapshot
Metal-Mediated Synthesis of Medium-Sized Rings
inferredcites →https://doi.org/10.1021/ja00019a027openalex-snapshot
A useful 12-I-5 triacetoxyperiodinane (the Dess-Martin periodinane) for the selective oxidation of primary or secondary alcohols and a variety of related 12-I-5 species
inferredcites →https://doi.org/10.1021/ja00276a062openalex-snapshot
Total synthesis of (.+-.)-fawcettimine (Burnell's base A)
inferredcites →https://doi.org/10.1021/ja01609a069openalex-snapshot
Approaches to the Total Synthesis of Adrenal Steroids. XII. dl-Δ5,16-3-Ethylenedioxypregnadiene-11,20-dione
inferredcites →https://doi.org/10.1021/ja046407bopenalex-snapshot
Total Synthesis of (−)-Strychnine
inferredcites →https://doi.org/10.1021/ja070259iopenalex-snapshot
Concise, Asymmetric, Stereocontrolled Total Synthesis of Stephacidins A, B and Notoamide B
inferredcites →https://doi.org/10.1021/ja101893bopenalex-snapshot
Total Synthesis of (+)-Complanadine A Using an Iridium-Catalyzed Pyridine C−H Functionalization
inferredcites →https://doi.org/10.1021/ja101956xopenalex-snapshot
Synthesis of (+)-Complanadine A, an Inducer of Neurotrophic Factor Excretion
inferredcites →https://doi.org/10.1021/ja103666nopenalex-snapshot
Total Synthesis of (+)-Sieboldine A
inferredcites →https://doi.org/10.1021/ja104575hopenalex-snapshot
Total Synthesis of (+)-Fastigiatine
inferredcites →https://doi.org/10.1021/ja107533mopenalex-snapshot
Synthesis of the Lycopodium Alkaloid (+)-Lycoflexine
inferredcites →https://doi.org/10.1021/ja109516fopenalex-snapshot
Concise Total Synthesis of (+)-Lyconadin A
inferredcites →https://doi.org/10.1021/ja992315oopenalex-snapshot
Tandem Radical Cyclizations Initiated with α-Carbonyl Radicals: First Total Synthesis of (+)-Paniculatine
inferredcites →https://doi.org/10.1021/jo00012a045openalex-snapshot
Unexpected behavior of dienol thio ethers gives versatile access to a large set of functionalized dienes
inferredcites →https://doi.org/10.1021/jo00268a015openalex-snapshot
Total synthesis of (.+-.)-fawcettimine
inferredcites →https://doi.org/10.1021/jo010122popenalex-snapshot
Ruthenium-Catalyzed Oxidative Cleavage of Olefins to Aldehydes
inferredcites →https://doi.org/10.1021/jo01110a606openalex-snapshot
Notes - Osmium Tetroxide-Catalyzed Periodate Oxidation of Olefinic Bonds
inferredcites →https://doi.org/10.1021/jo0483825openalex-snapshot
Structure Elucidation and Synthesis of Lycoposerramine-B, a Novel Oxime-ContainingLycopodiumAlkaloid fromLycopodium serratumThunb.
inferredcites →https://doi.org/10.1021/jo050423popenalex-snapshot
A General Enantioselective Approach to Jasmonoid Fragrances: Synthesis of (+)-(1R,2S)-Methyl Dihydrojasmonate and (+)-(1R,2S)-Magnolione
inferredcites →https://doi.org/10.1021/jo100499hopenalex-snapshot
Total Syntheses of (+)-Fawcettimine and (+)-Lycoposerramine-B
inferredcites →https://doi.org/10.1021/jo1023188openalex-snapshot
Application of the Helquist Annulation in Lycopodium Alkaloid Synthesis: Unified Total Syntheses of (−)-8-Deoxyserratinine, (+)-Fawcettimine, and (+)-Lycoflexine
inferredcites →https://doi.org/10.1021/jo200125copenalex-snapshot
An IMDAF Cycloaddition Approach toward the Synthesis of the Lycopodium Alkaloid (±)-Fawcettidine
inferredcites →https://doi.org/10.1021/ol100273popenalex-snapshot
Concise Total Synthesis of (±)-Lycopladine A
inferredcites →https://doi.org/10.1021/ol1009762openalex-snapshot
Enantiospecific Formal Total Synthesis of (+)-Fawcettimine
inferredcites →https://doi.org/10.1021/ol1012444openalex-snapshot
Total Synthesis of (−)-8-Deoxyserratinine via an Efficient Helquist Annulation and Double N-Alkylation Reaction
inferredcites →https://doi.org/10.1039/b409720nopenalex-snapshot
The Lycopodium alkaloids
inferredcites →https://doi.org/10.1039/b714078aopenalex-snapshot
Intermolecularradicaladdition reactions of α-iodo cycloalkenones and a synthetic study of the formal synthesis of enantiopurefawcettimine
inferredcites →https://doi.org/10.1039/b917965hopenalex-snapshot
Diversity-oriented synthesis of bicyclic and tricyclic alkaloids
inferredcites →https://doi.org/10.1039/np9910800455openalex-snapshot
The lycopodium alkaloids
inferredcites →https://doi.org/10.1055/s-1981-29377openalex-snapshot
Activated Dimethyl Sulfoxide: Useful Reagents for Synthesis
inferredcites →https://doi.org/10.1055/s-1990-21025openalex-snapshot
C-Acylation of Enolates by Methyl Cyanoformate: An Examination of Site- and Stereoselectivity
inferredcites →https://doi.org/10.1055/s-2002-25752openalex-snapshot
The Diels-Alder Reaction Selected Practical Methods
inferredcites →https://doi.org/10.1139/v63-452openalex-snapshot
LYCOPODIUM ALKALOIDS: PART VIII. NEW ALKALOIDS FROM JAMAICAN LYCOPODIUM SPECIES
inferredcites →https://doi.org/10.1139/v76-409openalex-snapshot
The alkaloids of L. magellanicum and the structure of magellanine
inferredcites →https://doi.org/10.1139/v89-163openalex-snapshot
Some new Lycopodium alkaloids
inferredcites →https://doi.org/10.1248/cpb.18.1880openalex-snapshot
Structure of Serratinidine and Fawcettidine. A New Type of Lycopodium Alkaloid
inferredcites →https://doi.org/10.1248/cpb.28.2394openalex-snapshot
Total syntheses of the lycopodium alkaloids (.+-.)-fawcettimine and (.+-.)-8-deoxyserratinine.
inferredcites →https://doi.org/10.3987/com-05-s(t)18openalex-snapshot
Improved Syntheses of the FR900482 and Mitomycin Benzazocine Ring Core via Mitsunobu Cyclization
inferredcites →https://doi.org/10.3987/rev-08-sr(f)6openalex-snapshot
The Lycopodium Alkaloids

What points at this work

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

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Phlegcarines A-C, three Lycopodium alkaloids from Phlegmariurus carinatus (Desv. ex Poir.) Ching
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Baeyer–Villiger (BV) Oxidation/Rearrangement in Organic Synthesis
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Total Synthesis of (−)‐Lycoposerramine‐S
inferred← citeshttps://doi.org/10.1002/ange.201306369openalex-snapshot
Divergent and Efficient Syntheses of the Lycopodium Alkaloids (−)‐Lycojaponicumin C, (−)‐8‐Deoxyserratinine, (+)‐Fawcettimine, and (+)‐Fawcettidine
inferred← citeshttps://doi.org/10.1002/ange.201409503openalex-snapshot
Total Syntheses of (−)‐Huperzine Q and (+)‐Lycopladines B and C
inferred← citeshttps://doi.org/10.1002/ange.202205439openalex-snapshot
Collective Total Syntheses of Five Lycopodium Alkaloids
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Total Synthesis of (−)‐Lycoposerramine‐S
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Divergent and Efficient Syntheses of the Lycopodium Alkaloids (−)‐Lycojaponicumin C, (−)‐8‐Deoxyserratinine, (+)‐Fawcettimine, and (+)‐Fawcettidine
inferred← citeshttps://doi.org/10.1002/anie.201409503openalex-snapshot
Total Syntheses of (−)‐Huperzine Q and (+)‐Lycopladines B and C
inferred← citeshttps://doi.org/10.1002/anie.202205439openalex-snapshot
Collective Total Syntheses of Five Lycopodium Alkaloids
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Divergent Total Syntheses of (−)‐Huperzine Q, (+)‐Lycopladine B, (+)‐Lycopladine C, and (−)‐4‐epi‐Lycopladine D
inferred← citeshttps://doi.org/10.1002/chem.201300364openalex-snapshot
Total Syntheses of (±)‐Fawcettimine, (±)‐Fawcettidine, (±)‐Lycoflexine, and (±)‐Lycoposerramine‐Q
inferred← citeshttps://doi.org/10.1002/chem.201303975openalex-snapshot
Heathcock‐Inspired Strategies for the Synthesis of Fawcettimine‐Type Lycopodium Alkaloids
inferred← citeshttps://doi.org/10.1002/tcr.201700047openalex-snapshot
Fawcettimine‐Type Lycopodium Alkaloids as a Driving Force for Discoveries in Organic Synthesis
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Synthesis of medium-sized benzo[b]azocines and benzo[b]azonines by photoinduced 8-/9-endo sulfonyl-cyclization
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Lycopodium Alkaloids – Synthetic Highlights and Recent Developments
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Tricyclic challenges: synthetic approaches toward dodecahydrocyclopenta[a]indenes
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Efficient synthesis of the cyclopentanone fragrances (Z)-3-(2-oxopropyl)-2-(pent-2-en-1-yl)cyclopentanone and Magnolione®
inferred← citeshttps://doi.org/10.1016/j.tet.2014.11.038openalex-snapshot
Total synthesis of (±)-lycoposerramine-R, a novel skeletal type of Lycopodium alkaloid
inferred← citeshttps://doi.org/10.1016/j.tet.2014.11.041openalex-snapshot
Enantioselective divergent total syntheses of fawcettimine-type Lycopodium alkaloids
inferred← citeshttps://doi.org/10.1016/j.tetasy.2017.07.004openalex-snapshot
Applications of sharpless asymmetric dihydroxylation in the total synthesis of natural products
inferred← citeshttps://doi.org/10.1016/j.tetlet.2020.152329openalex-snapshot
A concise asymmetric total synthesis of (+)-fawcettimine
inferred← citeshttps://doi.org/10.1021/acs.chemrev.7b00653openalex-snapshot
Divergent Strategy in Natural Product Total Synthesis
inferred← citeshttps://doi.org/10.1021/acs.chemrev.8b00583openalex-snapshot
Prevalence of Diarylprolinol Silyl Ethers as Catalysts in Total Synthesis and Patents
inferred← citeshttps://doi.org/10.1021/acs.joc.8b01719openalex-snapshot
Toward a Synthesis of Fawcettimine-Type Lycopodium Alkaloids: Stereocontrolled Synthesis of a Functionalized Azaspirocycle Precursor
inferred← citeshttps://doi.org/10.1021/acs.orglett.0c03386openalex-snapshot
Synthetic Study toward the Total Synthesis of Lycoclavatumide
inferred← citeshttps://doi.org/10.1021/acs.orglett.0c03816openalex-snapshot
Total Synthesis of Lyconesidine B, a Lycopodium Alkaloid with an Oxygenated, Amine-Type Fawcettimine Core
inferred← citeshttps://doi.org/10.1021/acs.orglett.1c00977openalex-snapshot
Concise Unified Access to (−)-8-Deoxy-13-dehydroserratinine, (+)-Fawcettimine, (+)-Fawcettidine, and (−)-8-Deoxyserratinine Using a Direct Intramolecular Reductive Coupling
inferred← citeshttps://doi.org/10.1021/acs.orglett.6b03416openalex-snapshot
Enantioselective Total Synthesis of (+)-Sieboldine A
inferred← citeshttps://doi.org/10.1021/acs.orglett.7b01154openalex-snapshot
Formal Total Synthesis of (±)-Lycojaponicumin C
inferred← citeshttps://doi.org/10.1021/acs.orglett.7b01633openalex-snapshot
Total Synthesis of Huperzine Q
inferred← citeshttps://doi.org/10.1021/acs.orglett.7b02122openalex-snapshot
Synthesis of Octahydro- and Decahydroquinolines by a One-Pot Cascade Reaction of Tetrasubstituted Enecarbamate
inferred← citeshttps://doi.org/10.1021/acs.orglett.9b00487openalex-snapshot
Double 1,3-Dipolar Cycloadditions of Two Nonstabilized Azomethine Ylides for Polycyclic Pyrrolidines
inferred← citeshttps://doi.org/10.1021/ja507016gopenalex-snapshot
Biogenetically Inspired Total Syntheses of Lycopodium Alkaloids, (+)-Flabellidine and (−)-Lycodine
inferred← citeshttps://doi.org/10.1021/jacs.6b13401openalex-snapshot
Total Synthesis of Lycopodium Alkaloids Palhinine A and Palhinine D
inferred← citeshttps://doi.org/10.1021/jo301545yopenalex-snapshot
Total Syntheses of (+)-Alopecuridine, (+)-Sieboldine A, and (−)-Lycojapodine A
inferred← citeshttps://doi.org/10.1021/jo3017555openalex-snapshot
Collective Synthesis of Lycopodium Alkaloids and Tautomer Locking Strategy for the Total Synthesis of (−)-Lycojapodine A
inferred← citeshttps://doi.org/10.1021/jo302333sopenalex-snapshot
Total Synthesis of the Lycopodium Alkaloid Serratezomine A Using Free Radical-Mediated Vinyl Amination to Prepare a β-Stannyl Enamine Linchpin
inferred← citeshttps://doi.org/10.1021/ol400628hopenalex-snapshot
Syntheses of (±)-Serratine, (±)-Lycoposerramine T, and (±)-Lycopoclavamine B
inferred← citeshttps://doi.org/10.1021/ol402906yopenalex-snapshot
Divergent Total Syntheses of (−)-Lycopladine D, (+)-Fawcettidine, and (+)-Lycoposerramine Q
inferred← citeshttps://doi.org/10.1021/ol403185gopenalex-snapshot
Stereocontrolled Total Syntheses of (±)-Fawcettimine, (±)-Lycoflexine, and (±)-Lycoflexine N-Oxide
inferred← citeshttps://doi.org/10.1021/ol4033495openalex-snapshot
Studies toward the Synthesis of Palhinine Lycopodium Alkaloids: A Morita–Baylis–Hillman/Intramolecular Diels–Alder Approach
inferred← citeshttps://doi.org/10.1021/ol500978kopenalex-snapshot
Isolation and Complete Structural Assignment of Lycopodium Alkaloid Cernupalhine A: Theoretical Prediction and Total Synthesis Validation
inferred← citeshttps://doi.org/10.1039/c4qo00353eopenalex-snapshot
Synthesis of (−)-mesembrine using the quaternary carbon-constructing allylic substitution
inferred← citeshttps://doi.org/10.1039/c5ob00827aopenalex-snapshot
The first asymmetric total synthesis of lycoposerramine-R
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PhI(OAc) 2 -mediated dialkoxylation of 4-aminostyrenes through a dearomatization process under metal-free conditions
inferred← citeshttps://doi.org/10.1039/d0ob02399jopenalex-snapshot
Synthesis of an isomer of lycoplanine A via cascade cyclization to construct the spiro-N,O-acetal moiety
inferred← citeshttps://doi.org/10.1039/d3ob01065aopenalex-snapshot
Total syntheses of macleanine and lycoposerramine-S
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New Lycopodium alkaloids from Phlegmariurus squarrosus
inferred← citeshttps://doi.org/10.1080/10286020.2015.1043281openalex-snapshot
Four new fawcettimine-related alkaloids fromPhlegmariurus squarrosus
inferred← citeshttps://doi.org/10.1246/bcsj.20220049openalex-snapshot
Total Synthesis of Lyconesidine B: Approach to a Three-Dimensional Tetracyclic Skeleton of Amine-Type Fawcettimine Core and Studies of Asymmetric Synthesis
inferred← citeshttps://doi.org/10.5059/yukigoseikyokaishi.73.1072openalex-snapshot
Recent Progress in Total Synthesis of Lycopodium Alkaloids
inferred← citeshttps://doi.org/10.5059/yukigoseikyokaishi.75.1035openalex-snapshot
Synthesis of Lycopodium Alkaloids
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Original article Assessment of antioxidative activity of alkaloids from Huperzia selago and Diphasiastrum complanatum using in vitro systems
inferred← citeshttps://doi.org/10.5530/ijpi.14.1.6openalex-snapshot
Recently Isolated Fawcettimine-Type Alkaloids
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Recent Advances on the Synthesis of Nine-Membered N-Heterocycles
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