Chemistry of O-Silylated Ketene Acetals : A Mild and Convenient Synthesis of β-Lactam Antibiotics

Yasuyuki KITA; Norio SHIBATA; Osamu TAMURA; Takashi MIKI

doi:10.1248/cpb.39.2225

北泰行, 柴田哲男, 田村修, 三木隆

著者情報

キーワード: O-silylated ketene acetal, intramolecular Pummerer-type reaction, 4-phenylthioazetidin-2-one, PS-5

ジャーナルフリー

1991 年 39 巻 9 号 p. 2225-2232

DOI https://doi.org/10.1248/cpb.39.2225

詳細

抄録

β-Amido sulfoxides (1) reacted with O-silylated ketene acetal (16) in dry acetonitrile in the presence of a catalytic amount of zinc iodide to give the 4-phenylthioazetidin-2-ones (17). Oxidation of 17 with m-chloroperbenzoic acid gave the corresponding sulfoxides (18), which were treated with 16 to give the azetidin-2-one esters (20), known precursors of PS-5-type carbapenem antibiotics.

責任著者(Corresponding author)

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