Studies on the total synthesis of lactacystin. An improved aldol coupling reaction and a β-lactone intermediate in thiol ester formation
EJ Corey, GA Reichard, R Kania
Index: Corey, E. J.; Reichard, Gregory, A.; Kania, Robert Tetrahedron Letters, 1993 , vol. 34, # 44 p. 6977 - 6980
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Citation Number: 81
Abstract
Abstract The recently developed total synthesis of lactacystin (1) has been improved by using the zirconium enolate derived from (R)-or (S)-2-siloxy-1, 2, 2-triphenylpropionate which lead stereospecifically to either (6S, 7R) or (6R, 7S) lactacystin, respectively. The formation of the thiol ester in the synthesis of 1 proceeds mainly via a β-lactone intermediate.
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