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a) For the preparation of an analogue of amphotericin B lacking the carboxylic acid group, see: M. Carmody, B. Murphy, B. Byrne, P. Power, D. Rai, B. Rawlings, P. Caffrey, J. Biol. Chem. 2005, 280, 34420-34426;
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b) A semisynthetic approach to this same molecule has also recently been reported: D.S. Palacios, T.M. Anderson, M. D. Burke, J. Am. Chem. Soc. 2007, 129, 13804-13805.
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For a preliminary report, see: a
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50
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We have previously disclosed full accounts of our gram scale syntheses of the C33-C38 fragment: J. Tholander, E. M, Carreira, HeIv. Chim. Acta 2001, 84, 613-622;
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We have previously disclosed full accounts of our gram scale syntheses of the C33-C38 fragment: J. Tholander, E. M, Carreira, HeIv. Chim. Acta 2001, 84, 613-622;
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51
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29044435380
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Professor Danishefsky suggested that diverted total synthesis could be used as way to perform molecular editing of undesired or unnecessary structural features of natural, products: R. M. Wilson, S. J. Danishefsky, J. Org. Chem. 2006, 71, 8329-8351
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Professor Danishefsky suggested that diverted total synthesis could be used as way to perform "molecular editing" of undesired or unnecessary structural features of natural, products: R. M. Wilson, S. J. Danishefsky, J. Org. Chem. 2006, 71, 8329-8351
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This method was reported by the McGarvey group in their synthetic studies towards amphotericin B (1) using a different homoallylic acohol. See: a) G. J. McGarvey, J.A. Mathys, K.J. Wilson, J. Org. Chem. 1996, 61, 5704-5705;
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This method was reported by the McGarvey group in their synthetic studies towards amphotericin B (1) using a different homoallylic acohol. See: a) G. J. McGarvey, J.A. Mathys, K.J. Wilson, J. Org. Chem. 1996, 61, 5704-5705;
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98
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67650697350
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NMR analysis of hemiketal 32 and 33 indicated that the expected anti product was formed.
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NMR analysis of hemiketal 32 and 33 indicated that the expected anti product was formed.
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a) N. K, Kochetkov, A. Y. Khorlin, A. F. Bochkov, Tetrahedron 1967, 23, 693-707;
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A related approach was recently published, see: H. Yu, D. L. Williams H, E. Ensley, Tetrahedron Lett. 2005, 46, 3417-3421; See also:
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a) A related approach was recently published, see: H. Yu, D. L. Williams H, E. Ensley, Tetrahedron Lett. 2005, 46, 3417-3421; See also:
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Glycoside tosylates have been reported to be capable of glycosidating simple alcohols: R. Eby, C. Schuerch, Carbohydr. Res. 1974, 34, 79-90.
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Glycoside tosylates have been reported to be capable of glycosidating simple alcohols: R. Eby, C. Schuerch, Carbohydr. Res. 1974, 34, 79-90.
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119
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67650694331
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Treating 53 with LiOH led to formation of a complex mixture of products. A complex mixture of byproducts is also formed during azide reduction with basic triethylamine and 1,3-propanedithiol, The base sensitivity of amphotericin B derivatives is highly dependant on structure. Chemical evidence in support of this supposition is the fact that while saponification of amphotericin B methyl, ester (AME) with LiOH proceeds cleanly, hydrolysis of the acetonide protected amphotericin B methyl ester leads to epimerization, presumably at C34.
-
Treating 53 with LiOH led to formation of a complex mixture of products. A complex mixture of byproducts is also formed during azide reduction with basic triethylamine and 1,3-propanedithiol, The base sensitivity of amphotericin B derivatives is highly dependant on structure. Chemical evidence in support of this supposition is the fact that while saponification of amphotericin B methyl, ester (AME) with LiOH proceeds cleanly, hydrolysis of the acetonide protected amphotericin B methyl ester leads to epimerization, presumably at C34.
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120
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53849121653
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V. Paquet, A. A. Volmer, E. M, Carreira, Chem. Eur. J. 2008, 14, 2465-2481
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123
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67650691168
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The width of the phospholipid bilayer of these LUVs is 37 Â and thus any formation of single barrel ion channels should be precluded. See supporting information for additional measurements.
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The width of the phospholipid bilayer of these LUVs is 37 Â and thus any formation of single barrel ion channels should be precluded. See supporting information for additional measurements.
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