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Las Vegas, Aug, ORGN 156. (b) Nicolaou, K. C.; Magolda, R.L. J. Org. Chem. 1981, 46, 1506. (c) Nicolaou, K. C.; Papahatjis, D. P.; Claremon, D. A.; Dolle, R. E. J. Am. Chem. Soc. 1981, 103, 6967. (d) Nicolaou, K. C.; Claremon, D. A.; Papahatjis, D. P.; Magolda, R.L. J. Am. Chem. Soc. 1981, 103, 6969
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(1) Preliminary communications: (a) Nicolaou, K. C.; Magolda, R.L., 2nd Chemical Congress of the North American Continent, Las Vegas, Aug, 1980; ORGN 156. (b) Nicolaou, K. C.; Magolda, R.L. J. Org. Chem. 1981, 46, 1506. (c) Nicolaou, K. C.; Papahatjis, D. P.; Claremon, D. A.; Dolle, R. E. J. Am. Chem. Soc. 1981, 103, 6967. (d) Nicolaou, K. C.; Claremon, D. A.; Papahatjis, D. P.; Magolda, R.L. J. Am. Chem. Soc. 1981, 103, 6969.
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(1980)
2nd Chemical Congress of the North American Continent
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Magolda, R.L.2
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(b) Westley, J. W. Adv. Appl. Microbiol. 1977, 22, 177. (c) Doblem, M. “Ionophores and their Structures”; Wiley-Interscience: New York, 1981. (d) Westley, J. W., Ed. “Polyether Antibiotics”; Marcel Dekker: New York, 1983; Vol. I and II
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(2) (a) Pressman, B. C. Annu. Rev. Biochem. 1976, 45, 501. (b) Westley, J. W. Adv. Appl. Microbiol. 1977, 22, 177. (c) Doblem, M. “Ionophores and their Structures”; Wiley-Interscience: New York, 1981. (d) Westley, J. W., Ed. “Polyether Antibiotics”; Marcel Dekker: New York, 1983; Vol. I and II.
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(b) Ireland, R. E.; Thaisrivongs, S.; Wilcox, C. S. J. Am. Chem. Soc. 1980, 102, 1155. (ce Ireland, R. E.; McGarvey, G. J.; Anderson, R., C.; Badoud, R.; Fitzimmons, B.; Thaisrivongs, S. J. Am. Chem. Soc. 1980, 102, 6178. Monensin: (d) Schmid, G.; Fukuyama, T.; Akasaka, K.; Kishi, Y. J. Am. Chem. Soc. 1979, 101, 259. (e) Fukuyama, T.; Wang, C.-L. J.; Kishi, Y. J. Am. Chem. Soc. 1979, 101, 260. (f) Fukuyama, T.; Akasaka, K.; Karanewsky, D. S.; Wang, C.-L. J.; Schmid, G.; Kishi, Y. J. Am. Chem. Soc. 1979, 101, 262. (g) Collum, D. D.; McDonald, J. H., III; Still, W. C. J. Am. Chem. Soc. 1980, 102, 2117, 2118, 2120. Calcimycin: (h) Evans, D. A.; Sacks, C. F.; Kleschick, W. C.; Taber, T. R. J. Am. Chem. Soc. 1979, 101, 6789. (i) Grieco, P. A.; Williams, E.; Tanaka, H.; Gilman, S. J. Org. Chem. 1980, 45, 3537. Narasin and salinomycin: (j) Kishi, Y.; Hatakeyama, S.; Lewis, M. D. In “Frontiers of Chemistry”;; Laidler, K. J., Ed.; Pergamon Press: New York, 1982; p 287. (4) The name indanomycin has recently been proposed for X-14547A: Edwards, M. P.; Ley, S. V.; Lister, S. G.; Palmer, B. D.; Williams, D. J., unpublished results. We thank Professor S. V. Ley for communicating this manuscript to us prior to publication
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(3) Lacalocid: (a) Nakata, T.; Schmid, G.; Vranesic, B.; Okigawa, M.; Smith-Palmer, T.; Kishi, Y. J. Am. Chem. Soc. 1978, 100, 2933. (b) Ireland, R. E.; Thaisrivongs, S.; Wilcox, C. S. J. Am. Chem. Soc. 1980, 102, 1155. (ce Ireland, R. E.; McGarvey, G. J.; Anderson, R., C.; Badoud, R.; Fitzimmons, B.; Thaisrivongs, S. J. Am. Chem. Soc. 1980, 102, 6178. Monensin: (d) Schmid, G.; Fukuyama, T.; Akasaka, K.; Kishi, Y. J. Am. Chem. Soc. 1979, 101, 259. (e) Fukuyama, T.; Wang, C.-L. J.; Kishi, Y. J. Am. Chem. Soc. 1979, 101, 260. (f) Fukuyama, T.; Akasaka, K.; Karanewsky, D. S.; Wang, C.-L. J.; Schmid, G.; Kishi, Y. J. Am. Chem. Soc. 1979, 101, 262. (g) Collum, D. D.; McDonald, J. H., III; Still, W. C. J. Am. Chem. Soc. 1980, 102, 2117, 2118, 2120. Calcimycin: (h) Evans, D. A.; Sacks, C. F.; Kleschick, W. C.; Taber, T. R. J. Am. Chem. Soc. 1979, 101, 6789. (i) Grieco, P. A.; Williams, E.; Tanaka, H.; Gilman, S. J. Org. Chem. 1980, 45, 3537. Narasin and salinomycin: (j) Kishi, Y.; Hatakeyama, S.; Lewis, M. D. In “Frontiers of Chemistry”;; Laidler, K. J., Ed.; Pergamon Press: New York, 1982; p 287. (4) The name indanomycin has recently been proposed for X-14547A: Edwards, M. P.; Ley, S. V.; Lister, S. G.; Palmer, B. D.; Williams, D. J., unpublished results. We thank Professor S. V. Ley for communicating this manuscript to us prior to publication.
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(b) Liu, C.-M.; Hermann, T. E.; Liu, M.; Bull, D. N.; Palleroni, N. J.; Prosser, B. L. T.; Westley, J. W.; Miller, P. A., J. Antibiot. 1979, 32, 95. (c) Westley, J. W.; Evans, R. H., Jr.; Sello, L. H.; Troupe, N.; Liu, C.-M.; Blount, J. F. J. Am. Chem. Soc. 1979, 32, 100. (d) Westley, J. W.; Liu, C.-M.; U.S. Patent 4100 171, 1978. (e) Westley, J. W., personal communication. (6) Story, P. R.; Burgess, J. R. Tetrahedron Lett. 1968, 1287
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(5) (a) Westley, J. W.; Evans, R. H., Jr.; Liu, C.-M.; Hermann, T.; Blount, J. F. J. Am. Chem. Soc. 1978, 100, 6786. (b) Liu, C.-M.; Hermann, T. E.; Liu, M.; Bull, D. N.; Palleroni, N. J.; Prosser, B. L. T.; Westley, J. W.; Miller, P. A., J. Antibiot. 1979, 32, 95. (c) Westley, J. W.; Evans, R. H., Jr.; Sello, L. H.; Troupe, N.; Liu, C.-M.; Blount, J. F. J. Am. Chem. Soc. 1979, 32, 100. (d) Westley, J. W.; Liu, C.-M.; U.S. Patent 4100 171, 1978. (e) Westley, J. W., personal communication. (6) Story, P. R.; Burgess, J. R. Tetrahedron Lett. 1968, 1287.
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(8) (a) Enders, D.; Eichenauer, H. Chem. Ber. 1979, 112, 2933; (b) Tetrahedron Lett. 1977, 191
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(7) Dauben, W. G.; Michmo, D. M. J. Org. Chem. 1977, 42, 682. (8) (a) Enders, D.; Eichenauer, H. Chem. Ber. 1979, 112, 2933; (b) Tetrahedron Lett. 1977, 191.
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(10) (a) Roush, W. R. J. Am. Chem. Soc. 1980, 102, 1390. (b) Roush, W. R. J. Org. Chem. 1979, 44, 4008. (11) (a) Bean, G. F. J. Heterocycl. Chem. 1965, 2, 473. (b) Hobbs, C. F.; McMillin, C. K.; Papadopoulos, E. P.; Vander Werf, C. A. J. Am. Chem. Soc. 1962, 84, 43.
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(b) Reich, H. J.; Chow, F.; Peake, S. L. Synthesis 1978, 299. (c) Nicolaou, K.; Magolda, R. L.; Sipio, W. J.; Barnette, W. E.; Lysenko, Z.; Joullie, M. M. J. Am. Chem. Soc. 1980, 102, 3784
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(13) (a) Nicolaou, K.C.; Barnette, W. E.; Gasic, G. P.; Magolda, R. L. J. Am. Chem. Soc. 1977, 99, 7736. (b) Reich, H. J.; Chow, F.; Peake, S. L. Synthesis 1978, 299. (c) Nicolaou, K.; Magolda, R. L.; Sipio, W. J.; Barnette, W. E.; Lysenko, Z.; Joullie, M. M. J. Am. Chem. Soc. 1980, 102, 3784.
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(14) Lavielle, S.; Borg, S.; Moreau, B.; Luche, M. J.; Marquet, A. J. Am. Chem. Soc. 1978, 100, 1558.
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(16) Kondo, K.; Tunemoto, D. Tetrahedron Lett. 1975, 1007. (17) Nicolaou, K. C.; Claremon, D. A.; Papahatjis, D. P. Tetrahedron Lett. 1981, 4, 647.
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(18) (a) Edwards, M. P.; Ley, S. V.; Lister, S. G. Tetrahedron Lett. 1981, 361. (b) Edwards, M. P.; Ley, S. V.; Lister, S. G.; Palmer, B. D. J. Chem. Soc., Chem. Commun. 1983, 630. (ce Edwards, M. P.; Ley, S. V.; Lister, S. G.; Palmer, B. D.; Williams, D. J., unpublished results. We thank Professor Ley for a preprint. (d) Roush, W. R.; Myers, A. G. J. Org. Chem. 1981, 46, 1509. (e) Roush, W. R.; Peseckis, S. M. Tetrahedron Lett. 1982, 4879; (f) Ho, P.-T. Can. J. Chem. 1982, 60, 90.
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