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1
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0035825071
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Taken in part from the Ph.D. Thesis of David Fernández, University of Barcelona, 2001. A preiminary report of portions of this work was presented in: (a) Álvarez, M.; Fernández, D.; Joule, J. A. Tetrahedron Lett. 2001, 42, 315-317.
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Tetrahedron Lett.
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Álvarez, M.1
Fernández, D.2
Joule, J.A.3
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2
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0041346193
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(b) Ahaidar, A.; Fernández, D.; Pérez, O.; Danelón, G.; Cuevas, C.; Manzanares, I.; Albericio, F.; Joule, J. A.; Álvarez, M. Tetrahedron Lett. 2003, 44, 6191-6194.
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Tetrahedron Lett.
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Ahaidar, A.1
Fernández, D.2
Pérez, O.3
Danelón, G.4
Cuevas, C.5
Manzanares, I.6
Albericio, F.7
Joule, J.A.8
Álvarez, M.9
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3
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0028198228
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Perry, N. B.; Ettouati, L.; Litaudon, M.; Blunt, J. W.; Munro, M. H. G.; Parkin, S.; Hope, H. Tetrahedron 1994, 50, 3987-3992.
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Tetrahedron
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Perry, N.B.1
Ettouati, L.2
Litaudon, M.3
Blunt, J.W.4
Munro, M.H.G.5
Parkin, S.6
Hope, H.7
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4
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0028230338
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Trimurtulu, G.; Faulkner, D. J.; Perry, N. B.; Ettouati, L.; Litaudon, M.; Blunt, J. W.; Munro, M. H. G.; Jameson, G. B. Tetrahedron 1994, 50, 3993-4000.
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Tetrahedron
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Trimurtulu, G.1
Faulkner, D.J.2
Perry, N.B.3
Ettouati, L.4
Litaudon, M.5
Blunt, J.W.6
Munro, M.H.G.7
Jameson, G.B.8
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5
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0035803049
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In the literature, two syntheses of variolin B and two syntheses of deoxyvariolin B, as well as several methods for the construction of the common tricyclic skeleton of these compounds, have also been reported: (a) Anderson, R. J.; Morris, J. C. Tetrahedron Lett. 2001, 42, 8697-8699.
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Anderson, R.J.1
Morris, J.C.2
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6
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0037462339
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(b) Molina, P.; Fresneda, P. M.; Delgado, S. J. Org. Chem. 2003, 68, 489-499.
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Molina, P.1
Fresneda, P.M.2
Delgado, S.3
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8
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84982062945
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(d) Capuano, L.; Schrepfer, H. J.; Müller, K.; Roos, H. Chem. Ber. 1974, 107, 929-936.
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Capuano, L.1
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Müller, K.3
Roos, H.4
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9
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0034660684
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(e) Fresneda, P. M.; Molina, P.; Delgado, S.; Bleda, J. A. Tetrahedron Lett. 2000, 41, 4777-4780.
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Fresneda, P.M.1
Molina, P.2
Delgado, S.3
Bleda, J.A.4
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10
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0345799614
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note
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4 at 100 °C, (e) TFA at reflux, (f) MsOH at 100 °C.
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13
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0005308199
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Charya, S. B.; Dutta, S.; Sanyal, U. J. Indian Chem. Soc. 1998, 75, 46-48.
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Charya, S.B.1
Dutta, S.2
Sanyal, U.3
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15
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0347060913
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note
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3 at reflux, (c) dry HCl in benzene with a Dean-Stark separator.
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18
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84986514837
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Girgis, M. S.; Larson, S. B.; Robins, R. K.; Cottam, H. B. J. Heterocycl. Chem. 1989, 26, 317-325.
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Girgis, M.S.1
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19
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84981776810
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Kühle, E.; Anders, B.; Zumach, G. Angew. Chem., Int. Ed. Engl. 1967, 6, 649-722.
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Kühle, E.1
Anders, B.2
Zumach, G.3
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20
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0020408669
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Merchan, F. L.; Garin, J.; Tejero, T. Synthesis 1982, 984-986. Potts, K. T.; Kuehnling, W. R.; Murphy, P. J. Org. Chem. 1984, 49, 2404-2407.
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Merchan, F.L.1
Garin, J.2
Tejero, T.3
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21
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0345799613
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Merchan, F. L.; Garin, J.; Tejero, T. Synthesis 1982, 984-986. Potts, K. T.; Kuehnling, W. R.; Murphy, P. J. Org. Chem. 1984, 49, 2404-2407.
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Potts, K.T.1
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23
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33845279743
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Potts, K. T.; Murphy, P. M.; Kuehnling, W. R. J. Org. Chem. 1988, 53, 2889-2898.
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Potts, K.T.1
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0006949441
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Houghten, R. A.; Simpson, R. A.; Hanson, R. N.; Rapoport, H. J. Org. Chem. 1979, 44, 4536-4543.
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Houghten, R.A.1
Simpson, R.A.2
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Rapoport, H.4
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27
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0000882277
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Andersen, K. K.; Bray, D. D.; Chumpradit, S.; Clark, M. E.; Habgood, G. J.; Hubbard. C. D.; Young K. M. J. Org. Chem. 1991, 56, 6508-6516.
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Andersen, K.K.1
Bray, D.D.2
Chumpradit, S.3
Clark, M.E.4
Habgood, G.J.5
Hubbard, C.D.6
Young, K.M.7
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30
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Heathcock, C. H.; Smith, K. M.; Blumenkofpf, T. A. J. Am. Chem. Soc. 1986, 108, 5022-5024.
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Schultz, A. G.; McCloskey, P. J.; Court, J. J. J. Am. Chem. Soc. 1987, 109, 6493-6502.
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0001244052
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Nagashima, H.; Ozaki, N.; Washiyama, M.; Itoh, K. Tetrahedron Lett. 1985, 26, 657-660.
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Nagashima, H.1
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Álvarez, M.; Fernández, D.; Joule, J. A. J. Chem. Soc., Perkin Trans. 1 2002, 471-475.
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Álvarez, M.1
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Joule, J.A.3
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36
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0346430690
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note
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Protection of the 9-amino group was important because the iodination of 12a gave an unidentified iodinated product that decomposed during attempted purification, presumably the result of iodine attack at the primary amine.
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37
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0001480207
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Majeed, A. J.; Antonsen, Φ.; Benneche, T.; Undheim, K. Tetrahedron 1989, 45, 993-1006. The preparation of 19 was improved-see Experimental Section.
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Majeed, A.J.1
Antonsen2
Benneche, T.3
Undheim, K.4
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38
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0347060911
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note
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Acetamide 20a and amine 20b could be separated by column chromatography. See Experimental Section.
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39
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0347060910
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Sawayama, T.; Yamamoto, R.; Kinugasa, H.; Nishimura, H. Heterocycles 1977, 8, 299-305.
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Sawayama, T.1
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Nishimura, H.4
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