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1
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(a) For a recent review of Diels-Alder cycloadditions and total synthesis, see: Nicolaou, K. C.; Snyder, S. A.; Montagnon, T.; Vassilikogiannakis, G. Angew. Chem., Int. Ed. 2002, 41, 1668.
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33846581559
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(b) For a recent example of Diels-Alder additions of substituted 1,2-naphthoquinones employed to access the steroid core, see: Gelman, D. M.; Mayes, P. A.; Mulder, R.; Perlmutter, P. Tetrahedron: Asymmetry 2006, 17, 3341.
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Gelman, D.M.1
Mayes, P.A.2
Mulder, R.3
Perlmutter, P.4
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9
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0001535003
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For a report on Lewis acid activation on the conjugate addition to 1,2-naphthoquinones, see: Naruta, Y. J. Am. Chem. Soc. 1980, 102, 3774.
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Naruta, Y.J.1
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4544233158
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2 activation of a Diels - Alder reaction with a 1,4-naphthoquinone dienophile see: Motoyoshiya, J.; Masue, Y.; Iwayama, G.; Yoshioka, S.; Nishii, Y.; Aoyama, H. Synthesis 2004, 2099.
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Synthesis
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Motoyoshiya, J.1
Masue, Y.2
Iwayama, G.3
Yoshioka, S.4
Nishii, Y.5
Aoyama, H.6
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11
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70350654006
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The isolated adducts were sufficiently stable for analysis but readily aromatized when stored at ambient temperature. Even when stored under inert atmosphere at -20°C (freezer), the aromatized product appeared after several days.
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The isolated adducts were sufficiently stable for analysis but readily aromatized when stored at ambient temperature. Even when stored under inert atmosphere at -20°C (freezer), the aromatized product appeared after several days.
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13
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70350685722
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note
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2/hexanes at -5 °C overnight.
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14
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1842713137
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For other X-ray crystal structures of cis-tetrahydrophenanthrenes, prepared by other means, see: (a) Bruyere, D.; Bouyssi, D.; Balme, G. Tetrahedron 2004, 60, 4007.
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(b) Duthaler, R. O.; Mathies, P.; Petter, W.; Heuberger, C.; Scherrer, V. Helv. Chim. Acta 1984, 67, 1217.
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Lin, Z.; Chen, J.; Valenta, Z. Tetrahedron Lett. 1997, 38, 3863.
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Lin, Z.1
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Pattenden, G.; Blake, A. J.; Reddy, L. K.; Stoker, D. A. Synlett 2006, 18, 3073.
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Pattenden, G.1
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(b) Gates, M.; Woodward, R. B.; Newhall, W. F.; Kunzli, R. J. Am. Chem. Soc. 1950, 72, 1141.
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Land, E. J.; Ramsden, C. A.; Riley, P. A.; Yogonathan, G. Tetrahedron 2003, 59, 9547.
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Land, E.J.1
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(a) Drexel, R. E.; Olack, G.; Jones, C.; Chumurny, G. N.; Santini, R.; Morrison, H. J. Org. Chem. 1990, 55, 2471.
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