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    Total synthesis of the epoxyquinol dimer (+)-panepophenanthrin: application of a diastereospecific biomimetic Diels–Alder dimerisation

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    Authors
    Comméiras, Laurent
    Moses, John E.
    Adlington, Robert M.
    Baldwin, Jack E.
    Cowley, Andrew R.
    Baker, Christopher M.
    Albrecht, Birgit
    Grant, Guy H.
    Issue Date
    2006
    Subjects
    total synthesis
    biomimetic synthesis
    stille coupling
    
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    Abstract
    An asymmetric total synthesis of the novel and structurally complex epoxyquinol natural product (+)-panepophenanthrin has been accomplished, in which a biomimetic Diels–Alder dimerisation is a key step. The key monomeric precursor was assembled by an efficient Stille cross coupling of two readily available building blocks that upon standing underwent a diastereospecific dimerisation cascade in excellent yield.
    Citation
    Commeiras, L., Moses, J.E., Adlington, R.M., Baldwin, J.E., Cowley, A.R., Baker, C.M., Albrecht, B. and Grant, G.H. (2006) 'Total synthesis of the epoxyquinol dimer (+)-panepophenanthrin: application of a diastereospecific biomimetic Diels–Alder dimerisation', Tetrahedron, 62(42),pp.9892-9901.
    Publisher
    Elsevier
    Journal
    Tetrahedron
    URI
    http://hdl.handle.net/10547/294635
    DOI
    10.1016/j.tet.2006.08.010
    Additional Links
    http://linkinghub.elsevier.com/retrieve/pii/S004040200601266X
    Type
    Article
    Language
    en
    ISSN
    00404020
    ae974a485f413a2113503eed53cd6c53
    10.1016/j.tet.2006.08.010
    Scopus Count
    Collections
    Cell and Cryobiology Research Group

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