Synthesis of Lysergic Acid Methyl Ester via the Double Cyclization Strategy

T Kurokawa, M Isomura, H Tokuyama, T Fukuyama

Index: Kurokawa, Toshiki; Isomura, Minetaka; Tokuyama, Hidetoshi; Fukuyama, Tohru Synlett, 2009 ,  # 5  p. 775 - 778

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Citation Number: 8

Abstract

The synthesis of the optically active nitroolefin 6 commenced with desymmetrization of meso-1,3-diol 7 (Scheme [²] ). Lipase PS-mediated acetylation at -15 ˚C afforded the optically active monoacetate, [8] which was immediately converted into BocNs-imide 8 [9] (95% ee) under the Mitsunobu conditions [¹0] to prevent racemization of the diol monoacetate. After removal of the Boc group, ozonolysis of the terminal olefin 9, followed by dehydration of the resulting ...