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Six-membered-ring-forming intramolecular Diels-Alder reactions of isobenzofurans proceed with exo stereochemistry as observed in ref 1. (a) Meegalla, S. K.; Rodrigo, R. Synthesis 1989, 942-944.
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For some recent references to synthesis of hydrophenanthrenes, including morphine alkaloids and abietanes, see: (a) Groth, U.; Richter, N.; Kalogerakis, A. Eur. J. Org. Chem. 2003, 4634-4639.
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(f) Majetich, G.; Liu, S.; Fang, J.; Siesel, D.; Zhang, Y. J. Org. Chem. 1997, 62, 6928-6951.
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Regioselectivity is controlled via steric effects
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Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford
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(a) Regioselectivity is controlled via steric effects. Wulff, W. D. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 5, pp 1065-1113.
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Wulff, W.D.1
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23144453570
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note
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(b) High regioselectivity in similar systems has been noted. See the examples in ref 1b and references therein.
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17
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(c) See also: Anderson, J. C.; Cran, J. W.; King, N. P. Tetrahedron Lett. 2002, 43, 3849-3852.
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Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Menucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowki, J.; Ortiz, J. V.; Stefanov, B. B. ; Liu, A.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, M.; Callacombe, M.; Gill, P. M. W.; Johnson, B. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian98; Gaussian, Inc.: Pittsburgh, PA, 1998.
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Clifford, S.24
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Petersson, G.A.26
Ayala, P.Y.27
Cui, Q.28
Morokuma, K.29
Malick, D.K.30
Rabuck, A.D.31
Raghavachari, K.32
Foresman, J.B.33
Cioslowki, J.34
Ortiz, J.V.35
Stefanov, B.B.36
Liu, A.37
Liashenko, A.38
Piskorz, P.39
Komaromi, I.40
Gomperts, R.41
Martin, R.L.42
Fox, D.J.43
Keith, T.44
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more..
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Harwood, L. M.; Jones, G.; Pickard, J.; Thomas, R. M.; Watkin, D. J. Chem. Soc., Chem. Commun. 1990, 605-607. Kinetic preference for the exo isomer was demonstrated using an α,β-unsaturated ketone as dienophile. Since the dienophile of intermediate 8g is devoid of the ketone group, and since the diene portion is an isobenzofuran, preference for the kinetic (exo) product is expected to be higher.
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Harwood, L.M.1
Jones, G.2
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Harwood, L. M.; Leeming, S. A.; Isaacs, N. S.; Jones, G.; Pickard, J.; Thomas, R. M.; Watkin, D. Tetrahedron Lett. 1988, 29, 5017-5020.
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Isaacs, N.S.3
Jones, G.4
Pickard, J.5
Thomas, R.M.6
Watkin, D.7
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85047700412
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For a general experimental see: Herndon, J. W.; Zhu, J.; Sampedro, D. Tetrahedron 2000, 56, 4985-4993.
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Herndon, J.W.1
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Sampedro, D.3
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25
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0001442424
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or Collective Volume 8, pp 216-219
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For a preparation of this compound see: Hegedus, L. S.; McGuire, M. A.; Schultze, L. M. Org. Synth. 1987, 65, 140-143, or Collective Volume 8, pp 216-219.
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