Chemistry of amphotericin B. Degradation studies and preparation of amphoteronolide B

KC Nicolaou, TK Chakraborty, Y Ogawa…

Index: Nicolaou; Chakraborty; Ogawa; Daines; Simpkins; Furst Journal of the American Chemical Society, 1988 , vol. 110, # 14 p. 4660 - 4672

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Citation Number: 69

Abstract

Abstract: Amphotericin B (1) was converted to a series of protected derivatives (3-5, 27). Compound 5 was degraded by ozonolysis and further elaborated to fragments 8, 14, and 15, three potential intermediates in a projected total synthesis of amphotericin B (1). A novel oxidative deglycosidation procedure based on radical bromination was devised and applied to the degradation of 5 and 27 to heptaenones 21 and 28, respectively. These ...