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1
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13244268408
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Carroll, A. R.; Hyde, E.; Smith, J.; Quinn, R. J.; Guymer, G.; Foster, P. I. J. Org. Chem. 2005, 70, 1096-1099.
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J. Org. Chem
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Carroll, A.R.1
Hyde, E.2
Smith, J.3
Quinn, R.J.4
Guymer, G.5
Foster, P.I.6
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3
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0001626504
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For brief reviews, see: a
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For brief reviews, see: (a) Overman, L. E. Acc. Chem. Res. 1992, 25, 352-359.
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(1992)
Acc. Chem. Res
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, pp. 352-359
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Overman, L.E.1
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4
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2942574530
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(b) Royer, J.; Bonin, M.; Micouin, L. Chem. Rev. 2004, 104, 2311-2352.
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(2004)
Chem. Rev
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Royer, J.1
Bonin, M.2
Micouin, L.3
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5
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33847087938
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Ito, Y.; Konoike, T,.; Harada, T.; Saegusa, T. J. Am. Chem. Soc. 1977, 99, 1487-1493.
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(1977)
J. Am. Chem. Soc
, vol.99
, pp. 1487-1493
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Ito, Y.1
Konoike, T.2
Harada, T.3
Saegusa, T.4
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7
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0033518612
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Brosius, A. D.; Overman, L. E.; Schwink, L. J. Am. Chem. Soc. 1999, 121, 700-709.
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(1999)
J. Am. Chem. Soc
, vol.121
, pp. 700-709
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Brosius, A.D.1
Overman, L.E.2
Schwink, L.3
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9
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0000238887
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For the use of this oxidant in phenolic couplings, see: a
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For the use of this oxidant in phenolic couplings, see: (a) Tobinaga, S.; Kotani, E. J. Am. Chem. Soc. 1972, 94, 309-310.
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(1972)
J. Am. Chem. Soc
, vol.94
, pp. 309-310
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Tobinaga, S.1
Kotani, E.2
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10
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0000867157
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In oxidative dimerization of ketones, see: b
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In oxidative dimerization of ketones, see: (b) Frazier, R. H.; Harlow, R. L. J. Org. Chem. 1980, 45, 5408-5411.
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(1980)
J. Org. Chem
, vol.45
, pp. 5408-5411
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Frazier, R.H.1
Harlow, R.L.2
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11
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45249123334
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This conversion was initially optimized with the dimethyl ester congener of 11. These studies showed that yields of the cyclized product were much lower using 2.0 equiv of LDA and 2.2 equiv of oxidant, or if Fe(acac) 3, FeCl3, Fe(cp)2PF6, or Cu(O 2CC5H11)2 was employed as the oxidant
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2 was employed as the oxidant.
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12
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0027260840
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For examples of intramolecular oxidative coupling of two different ketone enolates, see: (a) Cohen, T, McNamara, K, Kuzemko, M. A, Ramig, K, Landi, J. J, Jr, Dong, Y. Tetrahedron 1993, 49, 7931-7942
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For examples of intramolecular oxidative coupling of two different ketone enolates, see: (a) Cohen, T.; McNamara, K.; Kuzemko, M. A.; Ramig, K.; Landi, J. J., Jr.; Dong, Y. Tetrahedron 1993, 49, 7931-7942.
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13
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0000338089
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(b) Paquette, L. A.; Bzowej, E. I.; Branan, B. M.; Stanton, K. J. J. Org. Chem. 1995, 60, 7277-7283.
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(1995)
J. Org. Chem
, vol.60
, pp. 7277-7283
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Paquette, L.A.1
Bzowej, E.I.2
Branan, B.M.3
Stanton, K.J.4
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14
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33745685914
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Of ester and amide enolates, see: c
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Of ester and amide enolates, see: (c) Baran, P. S.; Hafensteiner, B. D.; Ambhaikar, N. B.; Guerrero, C. A.; Gallagher, J. D. J. Am. Chem. Soc. 2006, 128, 8678-8693.
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(2006)
J. Am. Chem. Soc
, vol.128
, pp. 8678-8693
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Baran, P.S.1
Hafensteiner, B.D.2
Ambhaikar, N.B.3
Guerrero, C.A.4
Gallagher, J.D.5
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15
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26844522419
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Immamoto, T.; Takiyama, N.; Nakamura, K.: Hatajima, T.; Kamiya, Y. J. Am. Chem. Soc. 1989, 111, 4392-4398.
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(1989)
J. Am. Chem. Soc
, vol.111
, pp. 4392-4398
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Immamoto, T.1
Takiyama, N.2
Nakamura, K.3
Hatajima, T.4
Kamiya, Y.5
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16
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45249111660
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The constitution and relative configuration of the α epimer was confirmed by single-crystal X-ray analysis
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The constitution and relative configuration of the α epimer was confirmed by single-crystal X-ray analysis.
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18
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45249108554
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Final purification of salt 17 by HPLC, as reported for the natural product,1 does not reproducibly give samples of 1 that show identical 1NMR spectra nor samples whose spectra precisely match those reported for natural 1 in DMSO-d6, we believe such samples are variable mixtures of zwitterionic 1 and salt 17. Addition of incremental amounts of sodium methylsulfinylmethylide-d 5 to hydrochloride salt 17 in DMSO-d6 revealed incremental shifts in most resonances. When ca. 1 equiv of base was added, a 1H NMR spectrum identical to that reported1 for natural 1 was obtained; see the Supporting Information for details. Unfortunately, a sample of natural actinophyllic acid is no longer available for direct comparison
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1 for natural 1 was obtained; see the Supporting Information for details. Unfortunately, a sample of natural actinophyllic acid is no longer available for direct comparison.
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