Tandem pericyclic reactions in a new FeCl3-promoted synthesis of catechol analogues of restrytisol C

N. F. Thomas, K. C. Lee, Thomas Paraidathathu, J. F F Weber, K. Awang, D. Rondeau, P. Richomme

    Research output: Contribution to journalArticle

    22 Citations (Scopus)

    Abstract

    The uncommon stilbene, 3,4-dimethoxy-12-acetoxy stilbene, has been synthesised by Heck coupling methodology in three steps. Treatment of this stilbene with ferric chloride in dichloromethane (room temperature) gave the unnatural stilbenoid dimers; 8,8′-(12,12′-bisacetoxyphenyl)-7′-(3′,4′- dimethoxyphenyl)-3,4-dimethoxy-7′,8′-dihydro-naphthalene and 8-(12-acetoxyphenyl)-8′-(12′-hydroxyphenyl)-7′-(3′, 4′-dimethoxyphenyl)-3,4-dimethoxy-7′,8′-dihydro- naphthalene. The structures of both stilbene dimers were unambiguously confirmed by 1D (1H, 13C) and 2D NMR experiments (COSY, HMQC, HMBC and NOESY). This is the first report of a FeCl3-promoted sequential pericyclic pathway leading to a highly oxygenated oligostilbenoid dimer (incorporating two asymmetric centres). The NMR spectroscopic evidence and a mechanistic interpretation consistent with these structures are discussed.

    Original languageEnglish
    Pages (from-to)7201-7206
    Number of pages6
    JournalTetrahedron
    Volume58
    Issue number36
    DOIs
    Publication statusPublished - 2 Sep 2002

    Fingerprint

    Stilbenes
    Dimers
    Nuclear magnetic resonance
    Methylene Chloride
    Temperature
    catechol
    Experiments
    naphthalene

    Keywords

    • Dihydronaphthalene
    • Ferric chloride
    • Pericyclic
    • Restrytisol
    • Stilbene

    ASJC Scopus subject areas

    • Biochemistry
    • Organic Chemistry
    • Drug Discovery

    Cite this

    Thomas, N. F., Lee, K. C., Paraidathathu, T., Weber, J. F. F., Awang, K., Rondeau, D., & Richomme, P. (2002). Tandem pericyclic reactions in a new FeCl3-promoted synthesis of catechol analogues of restrytisol C. Tetrahedron, 58(36), 7201-7206. https://doi.org/10.1016/S0040-4020(02)00798-6

    Tandem pericyclic reactions in a new FeCl3-promoted synthesis of catechol analogues of restrytisol C. / Thomas, N. F.; Lee, K. C.; Paraidathathu, Thomas; Weber, J. F F; Awang, K.; Rondeau, D.; Richomme, P.

    In: Tetrahedron, Vol. 58, No. 36, 02.09.2002, p. 7201-7206.

    Research output: Contribution to journalArticle

    Thomas, NF, Lee, KC, Paraidathathu, T, Weber, JFF, Awang, K, Rondeau, D & Richomme, P 2002, 'Tandem pericyclic reactions in a new FeCl3-promoted synthesis of catechol analogues of restrytisol C', Tetrahedron, vol. 58, no. 36, pp. 7201-7206. https://doi.org/10.1016/S0040-4020(02)00798-6
    Thomas NF, Lee KC, Paraidathathu T, Weber JFF, Awang K, Rondeau D et al. Tandem pericyclic reactions in a new FeCl3-promoted synthesis of catechol analogues of restrytisol C. Tetrahedron. 2002 Sep 2;58(36):7201-7206. https://doi.org/10.1016/S0040-4020(02)00798-6
    Thomas, N. F. ; Lee, K. C. ; Paraidathathu, Thomas ; Weber, J. F F ; Awang, K. ; Rondeau, D. ; Richomme, P. / Tandem pericyclic reactions in a new FeCl3-promoted synthesis of catechol analogues of restrytisol C. In: Tetrahedron. 2002 ; Vol. 58, No. 36. pp. 7201-7206.
    @article{a207c463e0cb4f449326a6711c8cbee7,
    title = "Tandem pericyclic reactions in a new FeCl3-promoted synthesis of catechol analogues of restrytisol C",
    abstract = "The uncommon stilbene, 3,4-dimethoxy-12-acetoxy stilbene, has been synthesised by Heck coupling methodology in three steps. Treatment of this stilbene with ferric chloride in dichloromethane (room temperature) gave the unnatural stilbenoid dimers; 8,8′-(12,12′-bisacetoxyphenyl)-7′-(3′,4′- dimethoxyphenyl)-3,4-dimethoxy-7′,8′-dihydro-naphthalene and 8-(12-acetoxyphenyl)-8′-(12′-hydroxyphenyl)-7′-(3′, 4′-dimethoxyphenyl)-3,4-dimethoxy-7′,8′-dihydro- naphthalene. The structures of both stilbene dimers were unambiguously confirmed by 1D (1H, 13C) and 2D NMR experiments (COSY, HMQC, HMBC and NOESY). This is the first report of a FeCl3-promoted sequential pericyclic pathway leading to a highly oxygenated oligostilbenoid dimer (incorporating two asymmetric centres). The NMR spectroscopic evidence and a mechanistic interpretation consistent with these structures are discussed.",
    keywords = "Dihydronaphthalene, Ferric chloride, Pericyclic, Restrytisol, Stilbene",
    author = "Thomas, {N. F.} and Lee, {K. C.} and Thomas Paraidathathu and Weber, {J. F F} and K. Awang and D. Rondeau and P. Richomme",
    year = "2002",
    month = "9",
    day = "2",
    doi = "10.1016/S0040-4020(02)00798-6",
    language = "English",
    volume = "58",
    pages = "7201--7206",
    journal = "Tetrahedron",
    issn = "0040-4020",
    publisher = "Elsevier Limited",
    number = "36",

    }

    TY - JOUR

    T1 - Tandem pericyclic reactions in a new FeCl3-promoted synthesis of catechol analogues of restrytisol C

    AU - Thomas, N. F.

    AU - Lee, K. C.

    AU - Paraidathathu, Thomas

    AU - Weber, J. F F

    AU - Awang, K.

    AU - Rondeau, D.

    AU - Richomme, P.

    PY - 2002/9/2

    Y1 - 2002/9/2

    N2 - The uncommon stilbene, 3,4-dimethoxy-12-acetoxy stilbene, has been synthesised by Heck coupling methodology in three steps. Treatment of this stilbene with ferric chloride in dichloromethane (room temperature) gave the unnatural stilbenoid dimers; 8,8′-(12,12′-bisacetoxyphenyl)-7′-(3′,4′- dimethoxyphenyl)-3,4-dimethoxy-7′,8′-dihydro-naphthalene and 8-(12-acetoxyphenyl)-8′-(12′-hydroxyphenyl)-7′-(3′, 4′-dimethoxyphenyl)-3,4-dimethoxy-7′,8′-dihydro- naphthalene. The structures of both stilbene dimers were unambiguously confirmed by 1D (1H, 13C) and 2D NMR experiments (COSY, HMQC, HMBC and NOESY). This is the first report of a FeCl3-promoted sequential pericyclic pathway leading to a highly oxygenated oligostilbenoid dimer (incorporating two asymmetric centres). The NMR spectroscopic evidence and a mechanistic interpretation consistent with these structures are discussed.

    AB - The uncommon stilbene, 3,4-dimethoxy-12-acetoxy stilbene, has been synthesised by Heck coupling methodology in three steps. Treatment of this stilbene with ferric chloride in dichloromethane (room temperature) gave the unnatural stilbenoid dimers; 8,8′-(12,12′-bisacetoxyphenyl)-7′-(3′,4′- dimethoxyphenyl)-3,4-dimethoxy-7′,8′-dihydro-naphthalene and 8-(12-acetoxyphenyl)-8′-(12′-hydroxyphenyl)-7′-(3′, 4′-dimethoxyphenyl)-3,4-dimethoxy-7′,8′-dihydro- naphthalene. The structures of both stilbene dimers were unambiguously confirmed by 1D (1H, 13C) and 2D NMR experiments (COSY, HMQC, HMBC and NOESY). This is the first report of a FeCl3-promoted sequential pericyclic pathway leading to a highly oxygenated oligostilbenoid dimer (incorporating two asymmetric centres). The NMR spectroscopic evidence and a mechanistic interpretation consistent with these structures are discussed.

    KW - Dihydronaphthalene

    KW - Ferric chloride

    KW - Pericyclic

    KW - Restrytisol

    KW - Stilbene

    UR - http://www.scopus.com/inward/record.url?scp=0037008944&partnerID=8YFLogxK

    UR - http://www.scopus.com/inward/citedby.url?scp=0037008944&partnerID=8YFLogxK

    U2 - 10.1016/S0040-4020(02)00798-6

    DO - 10.1016/S0040-4020(02)00798-6

    M3 - Article

    AN - SCOPUS:0037008944

    VL - 58

    SP - 7201

    EP - 7206

    JO - Tetrahedron

    JF - Tetrahedron

    SN - 0040-4020

    IS - 36

    ER -