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8.1: Road Maps in Total Synthesis of Natural Products

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    189881
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    Abyssomicin, Sorensen, 2006

    alkene addition

    carbonyl addition

    carboxylic substitution

    nucleophilic substitution

    oxidation of alcohols

    pericyclics

    Amphilectolide, Trauner, 2014

    carbonyl addition

    carbonyl reduction

    "Claisen condensation"-type carboxylic substitution

    cuprate addition

    ester reduction

    nitrile hydrolysis

    Annamoxic Acid, Corey, 2004

    alkene addition

    carbonyl addition

    elimination

    pericyclics

    Anominine, Nicolaou, 2012

    aldol reaction

    aliphatic nucleophilic substitution

    carbonyl addition

    carboxyl substitution

    elimination

    oxidation of alcohols

    radicals

    Aplykurodinone, Danishefsky, 2010

    aliphatic nucleophilic substitution

    carbonyl addition

    carboxylic substitution

    elimination

    oxidation of alcohols

    Atisine, Fukumoto, 1990

    esterification & amidification

    Michael addition

    reduction of esters

    Wittig & Horner-Wadsworth-Emmons reactions

    Aurantioclavine, Ellman, 2010

    aliphatic nucleophilic substitution

    carbonyl addition

    carboxylic substitution

    Aza-epothilone B, Danishefsky, 2000

    with bioassay study

    aliphatic nucleophilic substitution

    carbonyl addition

    carboxylic substitution

    Brevenal, Crimmins, 2010

    (partial synthesis)

    carbonyl addition, anionic & semianionic nucleophiles

    carbonyl addition, aldols

    carbonyl addition, ylides

    Brevetoxin, Crimmins, 2009

    aliphatic nucleophilic substitution

    electrophilic addition to alkenes

    carbonyl addition

    Briarellin, Crimmins, 2011

    nucleophilic addition to epoxide

    aliphatic nucleophilic substitution

    silyl protecting groups

    carboxylic substitution

    carbonyl addition

    electrophilic addition to alkenes

    ylide addition

    oxidation of alcohols

    Bryostatin, Burke, 2004

    dihydroxylation

    Horner-Wadsworth-Emmons or Wittig reaction

    hydroboration - oxidation

    oxidation of alcohols

    reduction of esters and ketones

    ring-closing olefin metathesis

    Callipeltoside, MacMillan, 2008

    aliphatic nucleophilic substitution

    electrophilic addition to alkenes

    carbonyl addition

    carboxylic substitution

    oxidation of alcohols

    Cassiol, Stoltz, 2008

    aliphatic nucleophilic substitution

    carbonyl addition

    carboxylic substitution

    Cavicularin, Beaudry, 2013

    Diels Alder

    etherification

    palladium coupling

    Wittig or Tebbe reactions

    Clavolonine, Fujioka, 2011

    aliphatic nucleophilic substitution and elimination

    Deoxytetracycline, Stork, 1996

    carbonyl addition (anionic and neutral nucleophiles)

    carboxylic substitution

    conjugate addition

    Dedihydrosemofalin, Overman, 2003

    alpha-alkylation

    aza-Cope rearrangement

    catalytic hydrogenation

    Diels Alder

    iminium ion formation

    oxidation of alcohols

    ozonolysis

    reduction of esters

    silylation of alcohols

    silylation of enolates

    silyl ether cleavage

    Wittig & Horner-Wadsorth-Emmons reactions

    Dendrobine, Carreira, 2012

    carbonyl addition

    carboxylic substitution

    Doliculide, Ghosh, 2001

    aliphatic nucleophilic substitution

    electrophilic addition to alkenes

    Dynemicin, Danishefsky, 1996

    aliphatic nucleophilic substitution

    alkene oxidation

    carbonyl addition

    carboxylic substitution

    elimination

    oxidation of alcohols

    pericyclics

    Echinopine, Nicolaou, 2010

    aliphatic nucleophilic substitution

    carbonyl addition

    carboxylic substitution

    Epothilone, Altmann, 2008

    aldol reaction

    alpha deprotonation

    Grignard reactions

    Wittig and Horner-Wadsworth-Emmons reactions

    Fischerindole, Baran, 2008

    aliphatic nucleophilic substitution

    carbonyl addition,

    carboxylic substitution,

    electrophilic addition to alkenes

    oxidation of alcohols

    radicals

    Ginkgolide, Corey, 1988

    aliphatic nucleophilic substitution

    carbonyl addition

    carboxylic substitution

    conjugate addition

    electrophilic addition to alkenes

    enolates

    rearrangements

    radicals

    Glucosylceramide, Overkleeft, 2007

    contains a bioassay exercise

    aliphatic nucleophilic substitution

    carbonyl addition

    carboxylic substitution

    elimination

    oxidation of alcohols

    Juvenile Hormone 1, Corey, 1968

    aliphatic nucleophilic substitution

    carbonyl addition

    carboxylic substitution

    cuprate addition

    electrophilic addition to alkenes

    oxidation of alcohols

    Wittig reaction

    Lepistine, Yokoshima & Fukuyama, 2014

    aliphatic nucleophilic substitution

    elimination

    Longifolene, Corey, 1961

    aliphatic nucleophilic substitution

    alkene oxidation

    carbonyl addition

    carboxylic substitution

    elimination

    oxidation of alcohols

    Lycopladine, Weinreb, 2015

    acetal/ketal cleavage

    acetal/ketal formation

    catalytic hydroformylation of alkenes

    Grignard reactions

    reductive amination

    Manzacidin A, Kawabata, 2013

    carboxylic substitution: esterification and amidification

    conjugate addition

    Nahuoic Acid, Smith, 2017

    acetal / ketal formation

    alkene reduction

    carbonyl reduction

    cuprate addition

    Diels Alder reaction

    epoxide opening (organometallic)

    ester hydrolysis

    keto-enol tautomerism

    methoxymethyl ether formation

    olefin metathesis

    silyl ether formation & cleavage

    syn dihydroxylation

    thioacetal / thioketal cleavage

    Nakadomarin, Kerr, 2007

    aliphatic nucleophilic substitution

    carbonyl addition

    carboxylic substitution

    conjugate addition

    elimination

    oxidation of alcohols

    Norzoanthamine, Theodorakis, 2011

    Robinson annulation

    conjugate addition

    anionic addition to carbonyls

    carboxylic substitution

    Octalactin, Buszek, 1994

    alkene reduction

    epoxidation

    hydroboration / oxidation

    Lindlar's catalyst

    silyl ether cleavage

    Okilactomycin, Smith, 2007

    aldol condensation

    aliphatic nucleophilic substitution

    carbonyl addition

    carboxylic substitution

    elimination

    oxidation of alcohols

    pericyclics

    Perhydrohistrionicotoxin, Corey, 1975

    aliphatic nucleophilic substitution

    carbonyl addition

    carboxylic substitution

    conjugate addition

    elimination

    enolates

    oxidation of alcohols

    radicals

    Periplanone, Still, 1979

    aldol condensation

    aliphatic nucleophilic substitution

    carbonyl addition

    carboxylic substitution,

    elimination

    oxidation of alcohols

    pericyclics

    Platensimicin, Ghosh, 2009

    aliphatic nucleophilic substitution

    electrophilic addition to alkenes

    Polyanthellin, Johnson, 2009

    electrophilic addition to alkenes: halogenation, hydroboration, oxymercuration, epoxidation, cyclopropanation

    aliphatic nucleophilic substitution

    Polycavernoside, Sasaki, 2017

    epoxidation

    epoxide ring-opening

    esterification

    oxidation of alcohols

    silyl ether cleavage

    Prostaglandin A2, Corey, 1972

    aliphatic nucleophilic substitution

    carbonyl addition

    carboxylic substitution

    elimination

    oxidation of alcohols

    Quinine, Stork, 2001

    aliphatic nucleophilic substitution

    carbonyl addition

    carboxylic substitution

    Quinocarcin, Stoltz, 2008

    carbonyl addition

    carboxylic substitution

    Salvileucalin, Reisman, 2011

    carbonyl addition

    carboxylic substitution

    Saxitoxin, Du Bois, 2006

    Contains a bioassay exercise.

    aliphatic nucleophilic substitution

    carbonyl addition

    carboxylic substitution

    electrophilic addition to alkenes

    oxidation of alcohols

    Scholarisine, Smith, 2012

    aliphatic nucleophilic substitution

    carbonyl addition

    carboxylic substitution,

    Serotobenine, Fukuyama & Kan, 2008

    aliphatic nucleophilic substitution

    alkene oxidation

    carbonyl addition

    carboxylic substitution

    elimination

    oxidation of alcohols

    pericyclics

    Solamine, Stark, 2006

    aliphatic nucleophilic substitution

    alkene oxidation

    carbonyl addition

    carboxylic substitution

    elimination

    oxidation of alcohols

    Spongidepsin, Cossy, 2006

    activation of carboxylic acids

    esterification & amidification

    Grignard reactions

    hydrolysis of amides

    reduction of esters

    Wittig & Horner-Wadsworth-Emmons reactions

    Strychnine, Overman, 1993

    aliphatic nucleophilic substitution

    alkene oxidation

    carbonyl addition

    carboxylic substitution

    conjugate addition

    elimination

    enolates

    Exercise: catalytic cycles in transition metal organometallics.

    Taiwaniaquinol, Fillion, 2005

    aldol condensation

    alpha alkylation

    conjugate addition

    electrophilic aromatic substitution

    etherification

    palladium coupling

    Taxol, Nicolaou, 1994

    aliphatic nucleophilic substitution

    alkene oxidation

    carbonyl addition

    carboxylic substitution

    elimination

    oxidation of alcohols

    pericyclics

    radicals

    Tetrodotoxin, Kishi, 1972

    aliphatic nucleophilic substitution

    alkene oxidation

    carbonyl addition

    carboxylic substitution

    electrophilic addition to alkenes

    oxidation of alcohols

    pericyclics

    rearrangements

    Tubingensin, Li, 2012

    carbonyl addition

    carboxylic substitution, aldol

    Tulearin, Cossy, 2009

    carbonyl addition, anionic & semianionic nucleophiles

    carbonyl addition, aldols

    carbonyl addition, ylides

    Vermiculine, Corey, 1975

    carbonyl addition

    carboxylic substitution

    Vibsanin, Takeo, 2015

    addition to carbonyl (organometallic)

    allylic substitution

    ester hydrolysis

    ester reduction

    esterification

    ether formation

    Mitsunobu reaction

    silyl ether formation and cleavage

    Wittig / Horner-Wadsworth-Emmons

    Vinigrol, Berriault, 2005

    acetals & ketals

    Claisen rearrangement

    Diels Alder

    syn-dihydroxylations

    esterification

    Grignard reagents

    hydride additions

    oxidation of alcohols

    silyl ethers

    Vittatalactone, Breit, 2010

    Aliphatic nucleophilic substitution

    Zaragozic acid, Nicolaou, 1994

    aliphatic nucleophilic substitution

    alkene oxidation

    carbonyl addition

    carboxylic substitution

    organo-transition metal reactions

    oxidation of alcohols

    radicals

    sulfur ylides

    Zincophorin, Hsung, 2007

    aliphatic nucleophilic substitution

    electrophilic addition to alkenes

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