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Tetrahedron letters

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

文献索引：Corey, E. J.; Reichard, Gregory, A.; Kania, Robert Tetrahedron Letters, 1993 , vol. 34, # 44 p. 6977 - 6980

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被引用次数: 81

摘要

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.

(R)-1,2,2-triphenyl-2-((trimethylsilyl)oxy)ethyl (2R,3S)-3-((4S,5S)-3-benzyl-4-(((tert-butyldimethylsilyl)oxy)methyl)-5-isopropyloxazolidin-4-yl)-3-hydroxy-2-methylpropanoate结构式

(R)-1,2,2-triph...

~%

(3R,4S,5S,6S)-1-Aza-5-(t-butyldimethylsilyloxymethyl)-4-hydroxy-6-isopropyl-3-methyl-7-oxabicyclo[3.3.0]-octan-2-one结构式

(3R,4S,5S,6S)-1...

(4R,5S)-3-benzyl-4-(((tert-butyldimethylsilyl)oxy)methyl)-5-isopropyloxazolidine-4-carbaldehyde结构式

(4R,5S)-3-benzy...

~%

(3R,4s,5r)-4-羟基-5-[(1s)-1-羟基-2-甲基丙基]-3-甲基-2-吡咯烷酮-5-羧酸结构式

(3R,4s,5r)-4-羟基...

(3R,4S,5S,6S)-1-Aza-5-(t-butyldimethylsilyloxymethyl)-4-hydroxy-6-isopropyl-3-methyl-7-oxabicyclo[3.3.0]-octan-2-one结构式

(3R,4S,5S,6S)-1...

~%

(3R,4s,5r)-4-羟基-5-[(1s)-1-羟基-2-甲基丙基]-3-甲基-2-吡咯烷酮-5-羧酸结构式

(3R,4s,5r)-4-羟基...

(R)-1,2,2-triphenyl-2-((trimethylsilyl)oxy)ethyl (2R,3S)-3-((4S,5S)-3-benzyl-4-(((tert-butyldimethylsilyl)oxy)methyl)-5-isopropyloxazolidin-4-yl)-3-hydroxy-2-methylpropanoate结构式

(R)-1,2,2-triph...

~%

(3R,4s,5r)-4-羟基-5-[(1s)-1-羟基-2-甲基丙基]-3-甲基-2-吡咯烷酮-5-羧酸结构式

(3R,4s,5r)-4-羟基...

Total synthesis of lactacystin

[Corey; Reichard, Gregory A. Journal of the American Chemical Society, 1992 , vol. 114, # 26 p. 10677 - 10678]

Total synthesis of lactacystin

[Corey; Reichard, Gregory A. Journal of the American Chemical Society, 1992 , vol. 114, # 26 p. 10677 - 10678]

Total synthesis of lactacystin

[Corey; Reichard, Gregory A. Journal of the American Chemical Society, 1992 , vol. 114, # 26 p. 10677 - 10678]

Total synthesis of lactacystin

[Corey; Reichard, Gregory A. Journal of the American Chemical Society, 1992 , vol. 114, # 26 p. 10677 - 10678]

Total synthesis of lactacystin

[Corey; Reichard, Gregory A. Journal of the American Chemical Society, 1992 , vol. 114, # 26 p. 10677 - 10678]