Practical total synthesis of (.+-.)-aklavinone and total synthesis of aklavin

…, JM McNamara, I Hasan, S Hatakeyama…

Index: Pearlman, B. A.; McNamara, J. M.; Hasan, I.; Hatakeyama, S.; Sekizaki, H.; Kishi, Y. Journal of the American Chemical Society, 1981 , vol. 103, # 14 p. 4248 - 4251

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Citation Number: 78

Abstract

Epoxidation of triol 13 (m-chloroperbenzoic acid, CH2C12, aqueous NaHC03 buffer) gave the epoxide 14 (mp 185-187 “C) in 90% yield. Oxidation of the alcohol (PCC, CH2C12, room temperature, 24 h) I4 gave 79% of the epoxy aldehyde 15 (mp 210-212 OC), Is which was separated from the aromatic impurity by preparative TLC. Sodium chlorite oxidation of aldehyde 15 (2 equiv of NH2S03H, dioxane, room temperature, 15 min) 16 followed by ...

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