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Kato, T.; Shizuri, Y.; Izumida, H.; Yokoyama, A.; Endo, M. Tetrahedron Lett. 1995, 36, 2133-2136.
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(a) Urban, S.; Leone, P. D. A.; Carroll, A. R.; Fechner, G. A.; Smith, J.; Hooper, J. N. A.; Quinn, R. J. J. Org. Chem. 1999, 64, 731-735.
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7
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0000292585
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(b) It should be noted that the same name was previously given to related, simpler pyrrole alkaloids: see: Bascombe, K. C.; Peter, S. R.; Tinto, W. F.; Bissada, S. M.; McLean, S.; Reynolds, W. F. Heterocycles 1998, 48, 1461-1464.
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Heterocycles
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Bascombe, K.C.1
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8
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0043208390
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note
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The absolute configuration of these natural products has not been determined unambiguously; however, the absolute stereochemistry of palau'amine (as shown in Figure 1) has been tenatively assigned on the basis of similarities of its CD spectrum with monobromophakellin hydrochoride (see ref 2a).
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9
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0043208391
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note
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50 of 42.8 nM in the mixed lymphocyte reaction (ref 2a).
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10
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0030802072
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(a) Overman, L. E.; Rogers, B. N.; Tellew, J. E.; Trenkle, W. C. J. Am. Chem. Soc. 1997, 119, 7159-7160.
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Overman, L.E.1
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(b) Starr, J. T.; Koch, G.; Carreira, E. M. J. Am. Chem. Soc. 2000, 122, 8793-8794.
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Starr, J.T.1
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12
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0042206092
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note
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(a) This biosynthetic proposal was suggested by a reviewer of the publication by Kinnel and Scheuer (see footnote 23, ref 2b).
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13
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0035136516
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(b) For a recently described unifying biosynthetic proposal of oroidin-derived metabolites, see: Mourabit, A. A.; Potier, P. Eur. J. Org. Chem. 2001, 237-243.
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Mourabit, A.A.1
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0001512880
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For related Diels-Alder reactions of vinyl imidazoles, see: Lovely, C.; Du, H.; Rasika Dias, H. V. Org. Lett. 2001, 3, 1319-1322.
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Lovely, C.1
Du, H.2
Rasika Dias, H.V.3
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17
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0019965054
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Dienophile 9 was synthesized from (S)-pyroglutamic acid (five steps) in analogy to reported procedures for related dienophiles; see: (a) Ohfune, Y.; Tomita, M. J. Am. Chem. Soc. 1982, 104, 3511-3513.
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0042206091
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note
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Current efforts are directed toward the presumed enantiomeric tricyclic core structure in order to utilize the less expensive (S)-pyroglutamic acid.
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20
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37049073710
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See also ref 12b.
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Sauter, R.; Thomas, E. J.; Watts, J. P. J. Chem. Soc., Perkin Trans. 1 1989, 519-523. See also ref 12b.
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Sauter, R.1
Thomas, E.J.2
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Baxter, R. L.; Camp, D. J.; Coutts, A.; Shaw, N. J. Chem. Soc., Perkin Trans. 1 1992, 255-258.
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Baxter, R.L.1
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Stonehouse, J.; Adell, P.; Keeler, J.; Shaka, A. J. J. Am. Chem. Soc. 1994, 116, 6037-6038.
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Stonehouse, J.1
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0043208384
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note
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See Supporting Information for details.
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0034658874
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We thank Dr. Eric Moher (Eli Lilly) for bringing this related work to our attention
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For a Baeyer-Villiger oxidation of an oxocarbenium ion, see: Hunt, K. W.; Grieco, P. A. Org. Lett. 2000, 2, 1717-1719. We thank Dr. Eric Moher (Eli Lilly) for bringing this related work to our attention.
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Hunt, K.W.1
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3OD)
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3OD): D'Ambrosio, M.; Guerriero, A.; Debitus, C.; Ribes, O.; Pusset, J.; Leroy, S.; Pietra, F. J. Chem. Soc., Chem. Commun. 1993, 1305-1306.
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D'Ambrosio, M.1
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Pietra, F.7
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6-DMSO): Tsuda, M.; Uemota, H.; Kobayashi, J. Tetrahedron Lett. 1999, 40, 5709-5712.
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Tsuda, M.1
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31
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0041705604
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note
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GOESY experiments shown were performed on spirocycle 20 and a deprotected derivative. See Supporting Information for details.
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32
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0043208388
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note
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Substantial quantities of aromatized byproducts were produced unless cyclohexene was added as an "alkene buffer". An example of this concept (unpublished results of J. J. Hans) was described to us recently by Professor T. R. Hoye.
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