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DOI: 10.1055/s-0030-1260073
One-Pot Synthesis of Fused-Tetracyclic Scaffolds Employing a Lewis Acid Promoted Domino Reaction of Naphthoquinones
Publikationsverlauf
Publikationsdatum:
16. Juni 2011 (online)
Abstract
The facile synthesis of tetracyclic molecular frameworks employing a Lewis acid promoted domino reaction of naphthoquinones with hydroxy- and amino-functionalized cross-conjugated trienes is reported. The reaction cascade involves a heterocyclization via hemiacetal or imine formation, and an intramolecular Diels-Alder cycloaddition.
Key words
tetracyclic scaffolds - naphthoquinone - Lewis acid promoted domino reaction - intramolecular Diels-Alder cycloaddition
- Supporting Information for this article is available online:
- Supporting Information
- 1
Zinzalla G.Thurston DE. Future Med. Chem. 2009, 1: 65 - 2
Bendiabdellah Y.Zinzalla G.Badarch U.Nahar KS.Antonow D.Rahman KM.Shoemaker RH.Melillo G.Thurston DE. Proceedings of the 100th Annual Meeting of the American Association for Cancer Research, San Diego, April 18-22, 2009 AACR; Philadelphia: 2009. p.4646 - 3
Park EJ.Kong D.Fisher R.Cardellina J.Shoemaker RH.Melillo G. Cell Cycle 2006, 5: 1847 -
4a
Ward DE.Abaee MS. Org. Lett. 2000, 2: 3937 -
4b
Ward DE.Souweha MS. Org. Lett. 2005, 7: 3533 -
4c
Souweha MS.Arab A.ApSimon M.Fallis AG. Org. Lett. 2007, 9: 615 -
4d
Souweha MS.Enright GD.Fallis AG. Org. Lett. 2007, 9: 5163 - 5
Nicolaou KC.Lim YH.Becker J. Angew. Chem. Int. Ed. 2009, 48: 3444 - 6
Grieco PA.Galatsis P.Spohn RF. Tetrahedron 1986, 42: 2847 - 7
Woo S.Squires N.Fallis AG. Org. Lett. 1999, 1: 573 -
10a
Grieco PA.Nunes JJ.Gaul MD. J. Am. Chem. Soc. 1990, 112: 4595 -
10b
Heydari A. Tetrahedron 2002, 58: 6777 -
11a
Stojanac Z.Dickinson RA.Stojanac N.Woznow RJ.Valenta Z. Can. J. Chem. 1975, 53: 616 -
11b
Kelly TR.Gillard JW.Goerner RN.Lyding JM. J. Am. Chem. Soc. 1977, 99: 5513 -
11c
Trost BM.Ippen J.Vladuchick WC. J. Am. Chem. Soc. 1977, 99: 8116 -
11d
Boeckman RK.Dolak TM.Culos KO. J. Am. Chem. Soc. 1978, 100: 7098 -
11e
Motoyoshiya J.Kameda T.Asari M.Miyamoto M.Narita S.Aoyama H.Hayashi S. J. Chem. Soc., Perkin Trans. 2 1997, 1845 - 12
Azumaya I.Uchida D.Kato T.Yokoyama A.Tanatani A.Takayanagi H.Yokozawa T. Angew. Chem. Int. Ed. 2004, 43: 1360 - 13
Ito M.Koo LW.Himizu A.Kobayashi C.Sakaguchi A.Ikariya T. Angew. Chem. Int. Ed. 2009, 48: 1324 - 14
Abraham E.Davies SG.Millican NL.Nicholson RL.Roberts PM.Smith AD. Org. Biomol. Chem. 2008, 6: 1655 - 15
Negro A.Garzon MJ.Martin JF.El Marini A.Roumestant ML.Lazaro R. Synth. Commun. 1991, 21: 359 - 16
Dose C.Seitz O. Bioorg. Med. Chem. 2008, 16: 65 - 17
Prevost C.Miginiac P.Miginiac-Groizeleau L. Bull. Soc. Chim. Fr. 1964, 2485 - 18
DeBoef B.Counts WR.Gilbertson SR. J. Org. Chem. 2007, 72: 799
References
The reactions were monitored by LC-MS and TLC on silica gel.
9The structures and relative stereochemistries were unambiguously assigned by 1D and 2D NMR experiments (including NOESY). Full characterization of the novel skeletons with their NMR data and spectra are included in the Supporting Information.