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The monoterpenoid indole alkaloids
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part 4: Saxton J. E., Ed.; Wiley: Chichester
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Recent reviews: (a) Herbert, R. B. The Monoterpenoid Indole Alkaloids, supplement to vol. 25, part 4 of The Chemistry of Heterocyclic Compounds: Saxton J. E., Ed.; Wiley: Chichester, 1994.
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The Chemistry of Heterocyclic Compounds
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Herbert, R.B.1
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Cordell, G. A., Ed.; Academic Press: New York, Chapter 9
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(c) Saxton, J. E. In The Alkaloids: Cordell, G. A., Ed.; Academic Press: New York, 1998; Vol. 50, Chapter 9.
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The Alkaloids
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Saxton, J.E.1
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Cordell, G. A., Ed.; Academic Press: New York. Chapter 1
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(d) Saxton, J. E. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: New York. 1998; Vol. 51, Chapter 1.
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The Alkaloids
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Academic Press: San Diego, CA
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(b) Sundberg, R. J. Indoles; Academic Press: San Diego, CA, 1996.
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Indoles
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Sundberg, R.J.1
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8
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0001426611
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Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Elsevier Science: Oxford
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(c) Sundberg, R. J. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Elsevier Science: Oxford, 1996; Vol. 2. pp 119-206.
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Sundberg, R.J.1
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9
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0000119323
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Kreher, R., Ed.; Georg Thieme Verlag: Stuttgart, Hetarene I, and references therein
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(d) Döpp, H.; Döpp, D.; Langer, U.; Gerding, B. In Methoden der Organischen Chemie; Kreher, R., Ed.; Georg Thieme Verlag: Stuttgart, 1994; Hetarene I, Teil 2, pp 546-1336, and references therein.
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Methoden der Organischen Chemie
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Döpp, H.1
Döpp, D.2
Langer, U.3
Gerding, B.4
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13
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0033594438
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and references therein
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(b) Tokuyama, H.; Yamashita, T.; Reding, M. T.; Kaburagi, Y.; Fukuyama. T. J. Am. Chem. Soc. 1999, 121, 3791-3792, and references therein.
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J. Am. Chem. Soc.
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Tokuyama, H.1
Yamashita, T.2
Reding, M.T.3
Kaburagi, Y.4
Fukuyama, T.5
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15
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0012114495
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Preparation of indoles via direct arylation of ketone enolates or their equivalents has been previously investigated. For example, see: (a) Kuehne, M. E. J. Am. Chem. Soc. 1962, 84, 837-847.
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(1962)
J. Am. Chem. Soc.
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Kuehne, M.E.1
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17
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0001440975
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(c) RajanBabu, T. V.; Reddy, G. S.; Fukunaga, T. J. Am. Chem. Sco. 1985, 107, 5473-5483.
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(1985)
J. Am. Chem. Sco.
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Rajanbabu, T.V.1
Reddy, G.S.2
Fukunaga, T.3
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18
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0001301160
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(d) RajanBabu, T. V.; Chenard, B. L.; Petti, M. A. J. Org. Chem. 1986, 51, 1704-1712.
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J. Org. Chem.
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Rajanbabu, T.V.1
Chenard, B.L.2
Petti, M.A.3
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19
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33751499126
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Phenylation of TMS enol ethers using diphenyl iodonium fluoride has been reported: Chen, K.; Koser, G. F. J. Org. Chem. 1991, 56, 5764-5767.
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(1991)
J. Org. Chem.
, vol.56
, pp. 5764-5767
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Chen, K.1
Koser, G.F.2
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20
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33947300284
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(a) House, H. O.; Czuba, L. J.; Gall, M.; Olmstead, H. G. J. Org. Chem. 1969, 34, 2324-2336.
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J. Org. Chem.
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House, H.O.1
Czuba, L.J.2
Gall, M.3
Olmstead, H.G.4
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21
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0033591157
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(b) Lessene, G.; Tripoli, R.; Cazeau, P.; Brian, C.; Bordeau, M. Tetrahedron Lett. 1999, 40, 4037-4040.
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Tetrahedron Lett.
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Lessene, G.1
Tripoli, R.2
Cazeau, P.3
Brian, C.4
Bordeau, M.5
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23
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0042073904
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(b) Orban, J.; Turner, J. V.; Twitchin, B. Tetrahedron Lett. 1984, 25, 5099-5102.
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Tetrahedron Lett.
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Orban, J.1
Turner, J.V.2
Twitchin, B.3
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28
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0042574911
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note
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2O (30 mL) was added the iodonium iodide (3.6 g, 7.9 mmol), and the mixture was stirred for several hours. After removal of the insoluble material by filtration, the solution was concentrated below 30°C under reduced pressure (<5 Torr). The residue was diluted with 8 mL of MeCN and crystallized at 0°C to give NPIF (1, 1.80 g first crop, 0.33 g second crop; total 2.13 g, 78%).
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29
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0001343241
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(a) Beringer, F. M.; Gindler, E. M.; Rapoport, M.; Taylor, R. J. J. Am. Chem. Soc. 1959, 81, 351-361.
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Beringer, F.M.1
Gindler, E.M.2
Rapoport, M.3
Taylor, R.J.4
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30
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0003041229
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(b) Beringer, F. M.; Forgione, P. S.; Yudis, M. D. Tetrahedron 1960, 8, 49-63.
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(1960)
Tetrahedron
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Beringer, F.M.1
Forgione, P.S.2
Yudis, M.D.3
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31
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0042073901
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note
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13C NMR and IR spectra. See Supporting Information for the spectral data as well as copies of actual spectra.
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32
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0042574913
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note
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The modest yield for this example stands in contrast with the high yield obtained for the o-nitrophenylation of a complex intermediate leading to the natural product tabersonine (ref 5).
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33
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85088810207
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note
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1H NMR) of cis-trans isomers.
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34
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0029936143
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Ghiron, C.; Piga, E.; Rossi, T.; Tamburini, B.; Thomas, R. J. Tetrahedron Lett. 1996, 37, 3891-3894.
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Tetrahedron Lett.
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Ghiron, C.1
Piga, E.2
Rossi, T.3
Tamburini, B.4
Thomas, R.J.5
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36
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37049090335
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(b) Moody, C. J.; Rahimtoola, K. F. J. Chem, Soc., Perkin Trans. 1 1990, 673-679.
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(1990)
J. Chem, Soc., Perkin Trans. 1
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Moody, C.J.1
Rahimtoola, K.F.2
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37
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0042574912
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note
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3N) to give the indole product (4).
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39
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0030908560
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Chen, C.; Lieberman, D. R.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. J. Org. Chem. 1997, 62, 2676-2677.
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J. Org. Chem.
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Chen, C.1
Lieberman, D.R.2
Larsen, R.D.3
Verhoeven, T.R.4
Reider, P.J.5
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