Copaene Synthesis Essay


Total synthesis of Copaene:
Reference:Heathcock, C. J. Am. Chem. Soc.1966, 88, 4112-4113. DOI
Keywords: Ketone → Ketal • O-H → O-SO2R • Alkyl-OH → Ketone • Epoxidation, peracid • Epoxide → Diol • Ketone enolate+Alkyl-X, Intram • O-Bn → O-H • Li-Alkyl+Ketone • Ketone+Li-Alkyl • Dehydration → Ene • Li-Me+Ketone • Ketone+Li-Alkyl • Hydrogenation Alkene • Dehydration → Ene •
Reagents:Glycol • Perbenzoic acid, 3-chloro • H2SO4 • DMSO (solvent) • HBr • Acetic acid • LiCHMe2 • CrO3, H2SO4 (Jones) • POCl3 • MeLi • H2, Pd • POCl3

Syntheses Home

Citation data is made available by participants in Crossref's Cited-by Linking service. For a more comprehensive list of citations to this article, users are encouraged to perform a search inSciFinder.

  • Synthesis of β-Bromo Glycerol Monoethers from α-Olefins

    SukhpritSinghAvinashBhadaniRamanKamboj

    Industrial & Engineering Chemistry Research200847 (21), 8090-8094

    Abstract | Full Text HTML | PDF | PDF w/ Links

  • Stereochemical Control of Reductions. 9. Haptophilicity Studies with 1,1-Disubstituted 2-Methyleneacenaphthenes

    Hugh W.Thompson andShaker Y.Rashid

    The Journal of Organic Chemistry200267 (9), 2813-2825

    Abstract | Full Text HTML | PDF | PDF w/ Links

  • Synthesis of a 2,7-Dioxatricyclo[4.2.1.03,8]nonane:  A Model Study for Possible Application in a Synthesis of Dictyoxetane

    Kelly A.Marshall,Anna K.Mapp, andClayton H.Heathcock

    The Journal of Organic Chemistry199661 (26), 9135-9145

    Abstract | Full Text HTML | PDF | PDF w/ Links

  • Through-bond interaction via cyclobutane relay orbitals as a means of extending conjugation. Synthesis of tricyclo[5.5.0.02,8]dodecatetraene, tricyclo[5.3.0.02,8]deca-3,5,9-triene, and 9,10-dimethylenetricyclo[5.3.0.02,8]deca-3,5-diene

    Juergen.DresselKent L.ChaseyLeo A.Paquette

    Journal of the American Chemical Society1988110 (16), 5479-5489

    Abstract | PDF | PDF w/ Links

  • Attraction and Electroantennogram Responses of Male Mediterranean Fruit Fly to Volatile Chemicals from Persea, Litchi and Ficus Wood

    JeromeNiogretWayne S.MontgomeryPaul E.KendraRobert R.HeathNancy D.Epsky

    Journal of Chemical Ecology201137 (5), 483-491

  • Reactions of Hydrazines with AlH 3 ·NMe 2 Et - Formation of Aluminum-Nitrogen Heterocycles

    WernerUhlAndreasVogelpohl

    European Journal of Inorganic Chemistry20092009 (1), 93-97

  • Development of a Host-Based Semiochemical Lure for Trapping Emerald Ash Borer Agrilus planipennis (Coleoptera: Buprestidae)

    Damon J.CrookAshotKhrimianJoseph A.FranceseIvichFraserTherese M.PolandAlan J.SawyerVictor C.Mastro

    Environmental Entomology200837 (2), 356-365

  • Development of a Host-Based Semiochemical Lure for Trapping Emerald Ash Borer Agrilus planipennis (Coleoptera: Buprestidae)

    Damon J.CrookAshotKhrimianJoseph A.FranceseIvichFraserTherese M.PolandAlan J.SawyerVictor C.Mastro

    Environmental Entomology200837, 356-365

  • Total Synthesis of Sequiterpenes

    Clayton H.Heathcock

    2007,197-558

  • Tandem Favorskii Intermediate/Cyclization Leading to Tricyclo[4.4.0.0]decanediones

    SasanKarimiJuliaChristodoulouGopalSubramaniam

    Synthetic Communications200636 (7), 929-934

  • The synthesis of [2.2.2]bicyclooctane and [3.1.1]bicycloheptane based amino acids as constrained glutamate analogues

    S.RichardBakerTimothy CHancox

    Tetrahedron Letters199940 (4), 781-784

  • A facile entry into the ring system of sativene

    SasanKarimiBrucePetersenKlaus G.GrohmannMichael D.BarnettLouisTodaro

    Tetrahedron Letters199839 (18), 2689-2692

  • Stereoselective Synthesis of Versatile Intermediates for Clerodanes Total synthesis

    Paul-HenriDucrotAnne-ClaireHervierJean-YvesLallemand

    Synthetic Communications199626, 4447-4457

  • Male lures for mediterranean fruitfly (Ceratitis capitata wied.): Structural analogs of α-copaene

    R. A.FlathR. T.CunninghamT. R.MonJ. O.John

    Journal of Chemical Ecology199420 (10), 2595-2609

  • Additional male mediterranean fruitfly (Ceratitis capitata wied.) Attractants from Angelica seed oil (Angelica archangelica L.)

    R. A.FlathR. T.CunninghamT. R.MonJ. O.John

    Journal of Chemical Ecology199420 (8), 1969-1984

  • Synthesis of 8-methyl-trans,trans-cyclodeca-3,7-dien-1β-ol and biotransformation into 4aβ-methyl-1,2,3,4,4a,5,6,7,8,8aα-decahydronaphthalene-1,7β-diol by Cichorium intybus.

    Dennis P.PietMaurice C.R.FranssenAedede Groot

    Tetrahedron199450 (10), 3169-3176

  • Alkylations of Enols and Enolates

    DruryCaine

    1991,1-63

  • A new path to the tricyclo[5.4.0.02,8]undecane skeleton.

    RolfGleiterGeorgMüllerUrsulaHuber-PatzHansRodewaldHermannIrngartinger

    Tetrahedron Letters198728 (18), 1985-1988

  • Tetracyclo[5.3.0.02,803,6]deca-4,9-diene. A new (CH)10 hydrocarbon

    RolfGleiterUlrichSteuerle

    Tetrahedron Letters198728 (49), 6159-6162

  • Simple syntheses of (±) -β-copaene, (±) -β-ylangene and lemnalol.

    Barry B.SniderYashwant S.Kulkarni

    Tetrahedron Letters198526 (46), 5675-5676

  • Stereochemische Untersuchungen zur Bildung von Naphtho-[1,2-b]furan-2-onen durch Hydrolyse von α,β-ungesättigten γ, Δ-Epoxysäureestern

    Norbert

  • Comments

    Leave a Reply

    Your email address will not be published. Required fields are marked *