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1
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0020336489
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For a recent review of these fascinating natural products, See
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For a recent review of these fascinating natural products, See: Daly, J.W. Fortschr. Chem. Org. Naturst. 1982, 41, 205-340.
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Daly, J.W.1
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0017601102
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Daly, J.W.; Witkop, B.; Tokuyama, T.; Nishikawa, T.; Karle, I.L. Helv. Chim. Acta 1977, 60, 1128-1140.
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Helv. Chim. Acta
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Daly, J.W.1
Witkop, B.2
Tokuyama, T.3
Nishikawa, T.4
Karle, I.L.5
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3
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0017834405
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Daly, J.W.; Brown, G.B.; Mensah-Dwunah, M.; Myers, C.W. Toxican, 1978, 16, 163-188.
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Toxican
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Daly, J.W.1
Brown, G.B.2
Mensah-Dwunah, M.3
Myers, C.W.4
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5
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84891751229
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Souccar, C.; Maleque, M.A.; Daly, J.W.; Albuquerque, E.X. Fed. Proc., Fed. Am. Soc. Exp. Biol. 1982, 41, 1299.
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Fed. Proc., Fed. Am. Soc. Exp. Biol.
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Souccar, C.1
Maleque, M.A.2
Daly, J.W.3
Albuquerque, E.X.4
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6
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0019790335
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For a total synthesis of (+)-gephyrotoxin, See:, There is current disagreement on the absolute configuration of the natural alkaloid.
-
For a total synthesis of (+)-gephyrotoxin, See: Fujimoto, R.; Kishi, Y. Tetrahedron Lett. 1981, 42, 4197-4198. There is current disagreement on the absolute configuration of the natural alkaloid.
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(1981)
Tetrahedron Lett.
, vol.42
, pp. 4197-4198
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Fujimoto, R.1
Kishi, Y.2
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7
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0019202868
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For previous total synthesis of (±)-gephyrotoxin, see
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For previous total synthesis of (±)-gephyrotoxin, see: Fujimoto, R.; Kishi, Y.J. Am. Chem. Soc. 1980, 102, 7154-7156.
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(1980)
Am. Chem. Soc.
, vol.102
, pp. 7154-7156
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Fujimoto, R.1
Kishi, Y.J.2
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9
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0006751710
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For a formal total synthesis, See
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For a formal total synthesis, See: Hart, D.J. J. Org. Chem. 1981, 46, 3576-3578.
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(1981)
J. Org. Chem.
, vol.46
, pp. 3576-3578
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Hart, D.J.1
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10
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0000273575
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For previous total syntheses of (±)-perhydrogephyrotoxin, See
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For previous total syntheses of (±)-perhydrogephyrotoxin, See: (a) Overman, L.E.; Fukaya, C. J. Am. Chem. Soc. 1980, 102, 1454-1456.
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(1980)
J. Am. Chem. Soc.
, vol.102
, pp. 1454-1456
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Overman, L.E.1
Fukaya, C.2
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12
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0042711408
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For syntheses of the racemic perhydropyrrolo[1, 2-a]quinoline ring system, See
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For syntheses of the racemic perhydropyrrolo[1, 2-a]quinoline ring system, See: Habermehl, G.G.; Thurau, O. Naturwissenschaften 1980, 67, 193.
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(1980)
Naturwissenschaften
, vol.67
, pp. 193
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Habermehl, G.G.1
Thurau, O.2
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14
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0020416580
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Warnick, J.E.; Jessup, P.J.; Overman, L.E.; Eldefrawri, M.E.; Nimit, Y.; Daly, J.W.; Albuquerque, E.X. Mol. Pharmacol, 1982, 22, 565-573.
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(1982)
Mol. Pharmacol
, vol.22
, pp. 565-573
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Warnick, J.E.1
Jessup, P.J.2
Overman, L.E.3
Eldefrawri, M.E.4
Nimit, Y.5
Daly, J.W.6
Albuquerque, E.X.7
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15
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0041892612
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Jessup, P.J.; Petty, C.B.; Roos, J.; Overman, L.E. Org. Synth. 1979, 59, 1-9.
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Org. Synth.
, vol.59
, pp. 1-9
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Jessup, P.J.1
Petty, C.B.2
Roos, J.3
Overman, L.E.4
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18
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0000802025
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Heathcock, C.H.; Kleinman, E.F.; Binkley, E.S. J. Am. Chem. Soc. 1982, 104, 1054-1068.
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J. Am. Chem. Soc.
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, pp. 1054-1068
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Heathcock, C.H.1
Kleinman, E.F.2
Binkley, E.S.3
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19
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0017302054
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Wenkert, E.; Chang, C.-J.; Chawla, H.P.S.; Cochran, D.W.; Hagaman, E.W.; King, J.C.; Orito, K.J. Am. Chem. Soc. 1976, 98, 3645-3655.
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Am. Chem. Soc.
, vol.98
, pp. 3645-3655
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Wenkert, E.1
Chang, C.-J.2
Chawla, H.P.S.3
Cochran, D.W.4
Hagaman, E.W.5
King, J.C.6
Orito, K.J.7
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20
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0015928593
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and ref 8a, b.
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Ziegler, F.E.; Spitzner, E.B. J. Am. Chem. Soc. 1973, 95, 7146-7149 and ref 8a, b.
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J. Am. Chem. Soc.
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, pp. 7146-7149
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Ziegler, F.E.1
Spitzner, E.B.2
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21
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33748542524
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For a review, See
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For a review, See: Johnson, F. Chem. Rev. 1968, 68, 375-413.
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(1968)
Chem. Rev.
, vol.68
, pp. 375-413
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Johnson, F.1
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22
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0346099920
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See: Matsumura, Y.; Maruoka, K.; Yamamoto, H. Tetrahedron Lett. 1982, 23, 1929-1932.
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(1982)
Tetrahedron Lett.
, vol.23
, pp. 1929-1932
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Matsumura, Y.1
Maruoka, K.2
Yamamoto, H.3
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23
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85022924645
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ref 3 and structure 1
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The numbering used for all intermediates corresponds to that of gephyrotoxin; see
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The numbering used for all intermediates corresponds to that of gephyrotoxin; see ref 3 and structure 1.
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25
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85022964223
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ref 8a
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A modification of this strategy, which culminated in the first synthesis of perhydrogephyrotoxin, is described in
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A modification of this strategy, which culminated in the first synthesis of perhydrogephyrotoxin, is described in ref 8a.
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26
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84982071481
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For related conversions of lactams to iminium ions (or the related enamines), See
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For related conversions of lactams to iminium ions (or the related enamines), See: Bohlmann, F.; Müller, H.-J.; Schumann, D. Chem. Ber. 1973, 106, 3026-3034.
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(1973)
Chem. Ber.
, vol.106
, pp. 3026-3034
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Bohlmann, F.1
Müller, H.-J.2
Schumann, D.3
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27
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0003282645
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Stevens, R.V.; Mehra, R.K.; Zimmerman, R.L. J. Chem. Soc., Chem. Commun. 1969, 877-878.
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(1969)
J. Chem. Soc., Chem. Commun.
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Stevens, R.V.1
Mehra, R.K.2
Zimmerman, R.L.3
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28
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0019775988
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Moos, W.H.; Gless, R.D.; Rapoport, H. J. Org. Chem. 1981, 46, 5064-5074.
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J. Org. Chem.
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, pp. 5064-5074
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Moos, W.H.1
Gless, R.D.2
Rapoport, H.3
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29
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85022909874
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Unpublished studies of Dr. Peter Jessup. The approach was identical with that described in ref 16
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Unpublished studies of Dr. Peter Jessup. The approach was identical with that described in ref 16.
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30
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37049091544
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Booth, H.; Griffiths, D.V.; Jozefowicz, M.L. J. Chem. Soc., Perkin Trans. 2. 1976, 751-760.
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J. Chem. Soc., Perkin Trans.
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Booth, H.1
Griffiths, D.V.2
Jozefowicz, M.L.3
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33847090061
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Vierhapper, F.W.; Eliel, E.L. J. Org. Chem. 1977, 42, 51-62; 1976, 41, 199-208.
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J. Org. Chem.
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Vierhapper, F.W.1
Eliel, E.L.2
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32
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0003909903
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The Chemistry of Organolithium Compounds
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Cf.:, Pergamon: Oxford, Chapter 1.
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Cf.: Wakefield, B.J. “The Chemistry of Organolithium Compounds”; Pergamon: Oxford, 1974; Chapter 1.
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(1974)
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Wakefield, B.J.1
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34
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85022944914
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A 20-cm DuPont Zorbax PSM-60 column and a 1:4 ethyl acetate/ hexane eluent were used for this analysis
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A 20-cm DuPont Zorbax PSM-60 column and a 1:4 ethyl acetate/ hexane eluent were used for this analysis.
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36
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85022962986
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These experiments were conducted by R. Freerks
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These experiments were conducted by R. Freerks.
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40
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33744586503
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Miyashita, M.; Yoshikoshi, A.; Grieco, P.A. J. Org. Chem. 1977, 42, 3772-3774.
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J. Org. Chem.
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, pp. 3772-3774
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Miyashita, M.1
Yoshikoshi, A.2
Grieco, P.A.3
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41
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84988103110
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(a) Deprotection under reductive conditions8b, 33b was markedly inferior. (b) Cf.
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(a) Deprotection under reductive conditions8b, 33b was markedly inferior. (b) Cf.: Just, G.; Grozinger, K. Synthesis 1976, 457-458.
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(1976)
Synthesis
, pp. 457-458
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Just, G.1
Grozinger, K.2
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45
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12644312578
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Mancuso, A.J.; Huang, S.-L.; Swern, D. J. Org. Chem. 1978, 43, 2480-2482.
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J. Org. Chem.
, vol.43
, pp. 2480-2482
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Mancuso, A.J.1
Huang, S.-L.2
Swern, D.3
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47
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0003036944
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Winkle, M.R.; Lansinger, J.M.; Ronald, R.C. J. Chem. Soc., Chem. Commun. 1980, 87-88.
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(1980)
J. Chem. Soc., Chem. Commun.
, pp. 87-88
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Winkle, M.R.1
Lansinger, J.M.2
Ronald, R.C.3
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49
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85022960182
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A 25-m SE-30 glass capillary column was used for this analysis
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A 25-m SE-30 glass capillary column was used for this analysis.
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52
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85022948486
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Multiple! resolved by resolution enhancement
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Multiple! resolved by resolution enhancement.
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