Total synthesis of the epoxyquinol dimer (+)-panepophenanthrin: application of a diastereospecific biomimetic Diels–Alder dimerisation
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Authors
Comméiras, LaurentMoses, John E.
Adlington, Robert M.
Baldwin, Jack E.
Cowley, Andrew R.
Baker, Christopher M.
Albrecht, Birgit
Grant, Guy H.
Issue Date
2006
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Show full item recordAbstract
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
ElsevierJournal
TetrahedronAdditional Links
http://linkinghub.elsevier.com/retrieve/pii/S004040200601266XType
ArticleLanguage
enISSN
00404020ae974a485f413a2113503eed53cd6c53
10.1016/j.tet.2006.08.010