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1
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0003031690
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Alkaloids: Chemical and Biological Perspectives
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Pelletier, S. W.; Ed.; Wiley: New York (b) Daly, J. W.; Myers, C. W.; Whittaker, N. Toxicon 1987, 25, 1023–1095. (c) Tokuyama, T.; Nishimori, N.; Shimada, A.; Edwards, M. W.; Daly, J. W. Tetrahedron 1987, 43, 643–652
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Daly, J. W.; Spande, T. F. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W.; Ed.; Wiley: New York, 1986; Vol. 4, Chapter 1, pp 1–274. (b) Daly, J. W.; Myers, C. W.; Whittaker, N. Toxicon 1987, 25, 1023–1095. (c) Tokuyama, T.; Nishimori, N.; Shimada, A.; Edwards, M. W.; Daly, J. W. Tetrahedron 1987, 43, 643–652.
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(1986)
, vol.4
, Issue.1
, pp. 1-274
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Daly, J.W.1
Spande, T.F.2
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2
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0018840172
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Indolizidine 223AB has been synthesized by more than one strategy, and its structure and absolute stereochemistry have been defined as (3R, 5R, 8aR)-3-butyl-5-propylindolizidine
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Hart, D. J.; Tsai, Y.-M. J. Org. Chem. 1982, 47, 4403–4409. (c) Broka, C. A.; Eng, K. K. J. Org. Chem. 1986, 51, 5043–5045. (d) Iida, H.; Watanabe, Y.; Kibayashi, C. J. Am. Chem. Soc. 1985, 107, 5534–5535. (e) Royer, J.; Husson, H.-P. Tetrahedron Lett. 1985, 26, 1515–1518.
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Indolizidine 223AB has been synthesized by more than one strategy, and its structure and absolute stereochemistry have been defined as (3R,5R,8aR)-3-butyl-5-propylindolizidine: (a) MacDonald, T. L. J. Org. Chem. 1980, 45, 193–194. (b) Hart, D. J.; Tsai, Y.-M. J. Org. Chem. 1982, 47, 4403–4409. (c) Broka, C. A.; Eng, K. K. J. Org. Chem. 1986, 51, 5043–5045. (d) Iida, H.; Watanabe, Y.; Kibayashi, C. J. Am. Chem. Soc. 1985, 107, 5534–5535. (e) Royer, J.; Husson, H.-P. Tetrahedron Lett. 1985, 26, 1515–1518.
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(1980)
J. Org. Chem.
, vol.45
, pp. 193-194
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MacDonald, T.L.1
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3
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0021172960
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Overman, L. E.; Goldstein, S. W. J. Am. Chem. Soc. 1984, 106, 5360–5361. (c) Overman, L. E.; Lin, N.-H. J. Org. Chem. 1985, 50, 3669–3670. (d) Overman, L. E.; Sharp, M. J. Tetrahedron Lett. 1988, 29, 901–904 (e) Daly, J. W.; McNeal, E. T.; Overman, L. E.; Ellison, D. H. J. Med. Chem. 1985, 28, 482–486. (f) Daly, J. W.; McNeal, E. M.; Gusovsky, F.; Ito, F.; Overman, L. E. J. Med. Chem. 1988, 31, 477–480.
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Overman, L. E.; Bell, K. L.; Ito, F. J. Am. Chem. Soc. 1984, 106, 4192–4201. (b) Overman, L. E.; Goldstein, S. W. J. Am. Chem. Soc. 1984, 106, 5360–5361. (c) Overman, L. E.; Lin, N.-H. J. Org. Chem. 1985, 50, 3669–3670. (d) Overman, L. E.; Sharp, M. J. Tetrahedron Lett. 1988, 29, 901–904. (e) Daly, J. W.; McNeal, E. T.; Overman, L. E.; Ellison, D. H. J. Med. Chem. 1985, 28, 482–486. (f) Daly, J. W.; McNeal, E. M.; Gusovsky, F.; Ito, F.; Overman, L. E. J. Med. Chem. 1988, 31, 477–480.
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(1984)
Am. Chem. Soc.
, vol.106
, pp. 4192-4201
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Overman, L.E.1
Bell, K.L.2
Ito, F.3
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4
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0004101860
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1,3-Dipolar Cycloaddition Chemistry
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Padwa, A., Ed.; Wiley-Interscience: New York Confalone, P. N.; Huie, E. M. Org. React. 1988, 36, 1–173. (b) For related intramolecular nitrone cycloadditions, see: Oppolzer, W.; Siles, S.; Snowden, R. L.; Bakker, B. H.; Petrzilka, M. Tetrahedron Lett. 1979, 20, 4391–4394. Oppolzer, W.; Siles, S.; Snowden, R. L.; Bakker, B. H.; Petrzilka, M. Tetrahedron 1985, 41, 3497–3509. Holmes, A. B.; Swithenbank, C.; Williams, S. F. J. Chem. Soc., Chem. Commun. 1986, 265–266
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Tufariello, J. J. In 1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; Wiley-Interscience: New York, 1984; Vol. 2, Chapter 12, pp 277–406. Confalone, P. N.; Huie, E. M. Org. React. 1988, 36, 1–173. (b) For related intramolecular nitrone cycloadditions, see: Oppolzer, W.; Siles, S.; Snowden, R. L.; Bakker, B. H.; Petrzilka, M. Tetrahedron Lett. 1979, 20, 4391–4394. Oppolzer, W.; Siles, S.; Snowden, R. L.; Bakker, B. H.; Petrzilka, M. Tetrahedron 1985, 41, 3497–3509. Holmes, A. B.; Swithenbank, C.; Williams, S. F. J. Chem. Soc., Chem. Commun. 1986, 265–266.
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(1984)
, vol.2
, Issue.12
, pp. 277-406
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Tufariello, J.J.1
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5
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84942705951
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186th National Meeting of the American Chemical Society
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Washington, D.C., August 28-September 2 ORGN 0123. Balasubramanian, N. Diss. Abstr. Int. B 1983, 44, 799. Balasubramanian, N. Chem. Abstr. 1983, 99, 212302u. Balasubramanian, N
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LeBel, N. A.; Balasubramanian, N. 186th National Meeting of the American Chemical Society: Washington, D.C., August 28-September 2, 1983; ORGN 0123. Balasubramanian, N. Diss. Abstr. Int. B 1983, 44, 799. Balasubramanian, N. Chem. Abstr. 1983, 99, 212302u. Balasubramanian, N. Org. Prep. Proced. Int. 1985, 17, 23–47.
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(1983)
Org. Prep. Proced. Int.
, Issue.17
, pp. 23-47
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LeBel, N.A.1
Balasubramanian, N.2
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8
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0001663505
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House, H. O.; Manning, D. T.; Melillo, D. G.; Lee, L. F.; Haynes, O. R.; Wilkes, B. E. J. Org. Chem. 1976, 41, 855–863.
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(1976)
J. Org. Chem.
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House, H.O.1
Manning, D.T.2
Melillo, D.G.3
Lee, L.F.4
Haynes, O.R.5
Wilkes, B.E.6
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10
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0019140070
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Pfenninger, J.; Heuberger, C.; Graf, W. Helv. Chim. Acta 1980, 63, 2328–2337.
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(1980)
Helv. Chim. Acta
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Pfenninger, J.1
Heuberger, C.2
Graf, W.3
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11
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85022485938
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Comparison of the synthetic material with an authentic sample (GC/MS) by Dr. T. Spande (NIH) showed the two to be identical and hence confirmed the assigned structure. (b) The synthetic sample was found to be identical with the natural material by NMR, IR, MS, and GC (Dr. J. W. Daly, personal communication)
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Comparison of the synthetic material with an authentic sample (GC/MS) by Dr. T. Spande (NIH) showed the two to be identical and hence confirmed the assigned structure. (b) The synthetic sample was found to be identical with the natural material by NMR, IR, MS, and GC (Dr. J. W. Daly, personal communication).
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12
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84985634005
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Felix, D.; Schreiber, J.; Ohloff, G.; Eschenmoser, A. Helv. Chim. Acta 1971, 54, 2896–2912.
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(1971)
Helv. Chim. Acta
, vol.54
, pp. 2896-2912
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Felix, D.1
Schreiber, J.2
Ohloff, G.3
Eschenmoser, A.4
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13
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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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(1978)
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Mancuso, A.J.1
Huang, S.L.2
Swern, D.3
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15
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0019774239
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A few α-chiral nitrones have been prepared and used in intramolecular cycloaddition reactions
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These were, however, C-alkenylnitrones and hence did not require the formation of α-chiral N-alkenylhydroxylamines. See Baggiolini, E. G.; Lee, H. L.; Pizzolato, G.; Uskoković, M. R. J. Am. Chem. Soc. 1982, 104, 6460–6462
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A few α-chiral nitrones have been prepared and used in intramolecular cycloaddition reactions. These were, however, C-alkenylnitrones and hence did not require the formation of α-chiral N-alkenylhydroxylamines. See: Wovkulich, P. M.; Uskoković, M. R. J. Am. Chem. Soc. 1981, 103, 3958–3959. Baggiolini, E. G.; Lee, H. L.; Pizzolato, G.; Uskoković, M. R. J. Am. Chem. Soc. 1982, 104, 6460–6462.
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J. Am. Chem. Soc.
, vol.103
, pp. 3958-3959
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Wovkulich, P.M.1
Uskoković, M.R.2
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18
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0001038585
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Cuprate displacement of tosvlate
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The aldehyde 32 was found to be in the form of the corresponding hemi-aminal. (c) Wittig olefination: Greenwald, R.; Chaykovsky, M.; Corey, E. J. J. Org. Chem. 1963, 28, 1128–1129.
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Cuprate displacement of tosvlate: Johnson, C. R.; Dutra, G. A. J. Am. Chem. Soc. 1973, 95, 7777–7782, 7783–7788. (b) The aldehyde 32 was found to be in the form of the corresponding hemi-aminal. (c) Wittig olefination: Greenwald, R.; Chaykovsky, M.; Corey, E. J. J. Org. Chem. 1963, 28, 1128–1129.
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(1973)
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, vol.95
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Johnson, C.R.1
Dutra, G.A.2
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