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Volumn 105, Issue 7, 1983, Pages 1988-2006

The Total Synthesis of Ionophore Antibiotics. A Convergent Synthesis of Lasalocid A (X537A)

Author keywords

[No Author keywords available]

Indexed keywords

LASALOCID;

EID: 0020605141     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00345a055     Document Type: Article
Times cited : (203)

References (32)
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    • The authors express their grateful appreciation for the support of this group by a grant from NIH, Grant HL-23167. Grateful acknowledgement is also made for use of the Southern California Regional NMR Facility (National Science Foundation Grant CHE-79-16324). It is a particular pleasure to acknowledge the support of the Hoffmann-LaRoche Foundation through a grant and the late Willy Leimgruber, Director of Chemical Research, for his moral support and supplies of Lasalocid A
    • The authors express their grateful appreciation for the support of this group by a grant from NIH, Grant HL-23167. Grateful acknowledgement is also made for use of the Southern California Regional NMR Facility (National Science Foundation Grant CHE-79-16324). It is a particular pleasure to acknowledge the support of the Hoffmann-LaRoche Foundation through a grant and the late Willy Leimgruber, Director of Chemical Research, for his moral support and supplies of Lasalocid A.
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    • NRC (Canada) Postdoctoral Fellow, 1978-1979; NSERC (Canada)-NATO Postdoctoral Fellow, 1979-1980.
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    • Lasalocid A: Isolation-Berger, J.; Rochlin, A.I.; Scott, W.E.; Steinbach, L.H.; Goldberg, M.W. J. Am. Chem. Soc. 1951, 73, 5295-5298. Structure-Westley, J.W.; Evans, R.H., Jr.; Pruess, D.L.; Stempel, A. Chem. Commun. 1970, 1467-1468. Johnson, S.M.; Herrin, J.; Liu, S.J.; Paul, I.C.J. Am. Chem. Soc. 1970, 92, 4428-4435.
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    • Calcimycin:, Grieco, P.A.; Williams, E.; Tanaka, H.; Gilman, S.J. Org. Chem. 1980, 45, 3537-3539. Lasalocid A: Nakata, T.; Schmid, G.; Vranesic, B.; Okigawa, M.; Smith-Palmer, T.; Kishi, Y.J. Am. Chem. Soc. 1978, 100, 2933-2935. Monensin: Fukuyama, T.; Akasaka, K.; Karanewsky, D.S.; Wang, C.-L.J.; Schmid, G.; Kishi, Y.J. Am. Chem. Soc. 1979, 101, 259-263. Still, W.C.; McDonald, J.; Collum, D.J. Am. Chem. Soc. 1980, 102, 2117-2121.
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    • For preliminary reports of this work, See:, Ireland, R.E.; McGarvey, G.J.; Anderson, R.C.; Badoud, R.; Fitzsimmons, B.J.; Thaisrivongs, S.J. Am. Chem. Soc. 1980, 102, 6178-6180.
    • For preliminary reports of this work, See: Ireland, R.E.; Thaisrivongs, S.; Wilcox, C.S. J. Am. Chem. Soc. 1980, 102, 1155-1157. Ireland, R.E.; McGarvey, G.J.; Anderson, R.C.; Badoud, R.; Fitzsimmons, B.J.; Thaisrivongs, S.J. Am. Chem. Soc. 1980, 102, 6178-6180.
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    • Lasalocid A numbering system is used throughout this discussion for clarity
    • Lasalocid A numbering system is used throughout this discussion for clarity.
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    • Subsequent to the current work, a definitive determination for the boat-like character for the transition state for rearrangement of glycal silyl ketene acetals was made through the synthesis of the (+)- and (-)-nonactic acids
    • Subsequent to the current work, a definitive determination for the boat-like character for the transition state for rearrangement of glycal silyl ketene acetals was made through the synthesis of the (+)- and (-)-nonactic acids (Ireland, R.E.; Vevert, J.-P. Can. J. Chem. 1981, 59, 572-583).
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    • Unpublished results from this laboratory by L. Courtney
    • Unpublished results from this laboratory by L. Courtney.
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