Total synthesis of lactacystin

EJ Corey, GA Reichard

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

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Citation Number: 164

Abstract

Lactacystin (1) is a novel microbial product which was identified by Omura et al. after screening several thousand culture samples for the capacity to induce differentiation in a neuroblastoma cell line.'-* The great current interest in neurotrophic proteins, eg, nerve growth factor, as therapeutic agents and neuroscience research tools3” and the scarcity of 1 encouraged us to undertake the synthesis which is described herein. The availability of ...

 Related Synthetic Route
(4R,5S)-3-benzyl-4-(((tert-butyldimethylsilyl)oxy)methyl)-5-isopropyloxazolidine-4-carbaldehyde Structure

145484-22-6

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

~%

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

145451-95-2

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

tert-Butyldimethylsilyl chloride Structure

18162-48-6

tert-Butyldimet...

~%

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

145451-95-2

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

METHYL (2R,3S)-2-BENZYLAMINO-3-HYDROXY-2-HYDROXYMETHYL-4-METHYLPENTANOATE Structure

145451-91-8

METHYL (2R,3S)-...

~%

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

145451-95-2

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

methyl (2R,4R)-3-benzyl-2-tert-butyl-4-[(1S)-1-hydroxy-2-methylpropyl]-1,3-oxazolidine-4-carboxylate Structure

145451-90-7

methyl (2R,4R)-...

~%

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

145451-95-2

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

(4R,5S)-N-Benzyl-4-(t-butyldimethylsilyloxymethyl)-4-hydroxymethyl-5-isopropyloxazoladine Structure

145452-01-3

(4R,5S)-N-Benzy...

~%

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

145451-95-2

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

methyl (4R,5S)-3-benzyl-4-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-propan-2-yl-1,3-oxazolidine-4-carboxylate Structure

145451-93-0

methyl (4R,5S)-...

~%

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

145451-95-2

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

tert-Butyldimethylsilyl chloride Structure

18162-48-6

tert-Butyldimet...

~%

(4R,5S)-N-Benzyl-4-(t-butyldimethylsilyloxymethyl)-4-hydroxymethyl-5-isopropyloxazoladine Structure

145452-01-3

(4R,5S)-N-Benzy...

methyl (2R,4R)-3-benzyl-2-tert-butyl-4-[(1S)-1-hydroxy-2-methylpropyl]-1,3-oxazolidine-4-carboxylate Structure

145451-90-7

methyl (2R,4R)-...

~%

(4R,5S)-N-Benzyl-4-(t-butyldimethylsilyloxymethyl)-4-hydroxymethyl-5-isopropyloxazoladine Structure

145452-01-3

(4R,5S)-N-Benzy...

METHYL (2R,3S)-2-BENZYLAMINO-3-HYDROXY-2-HYDROXYMETHYL-4-METHYLPENTANOATE Structure

145451-91-8

METHYL (2R,3S)-...

~%

(4R,5S)-N-Benzyl-4-(t-butyldimethylsilyloxymethyl)-4-hydroxymethyl-5-isopropyloxazoladine Structure

145452-01-3

(4R,5S)-N-Benzy...

methyl (2R,4R)-3-benzyl-2-tert-butyl-4-[(1S)-1-hydroxy-2-methylpropyl]-1,3-oxazolidine-4-carboxylate Structure

145451-90-7

methyl (2R,4R)-...

~91%

METHYL (2R,3S)-2-BENZYLAMINO-3-HYDROXY-2-HYDROXYMETHYL-4-METHYLPENTANOATE Structure

145451-91-8

METHYL (2R,3S)-...

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

145451-95-2

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

~92%

(3R,4S,5R,6S)-1-AZA-4-HYDROXY-5-HYDROXYMETHYL-6-ISOPROPYL-3-METHYL-7-OXABICYCL[3.3.0]OCTAN-2-ONE Structure

145452-02-4

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

METHYL (2R,3S)-2-BENZYLAMINO-3-HYDROXY-2-HYDROXYMETHYL-4-METHYLPENTANOATE Structure

145451-91-8

METHYL (2R,3S)-...

~%

(3R,4S)-(-)-1-BENZYL-3,4-PYRROLIDINDIOL Structure

145451-97-4

(3R,4S)-(-)-1-B...

methyl (2R,4R)-3-benzyl-2-tert-butyl-4-[(1S)-1-hydroxy-2-methylpropyl]-1,3-oxazolidine-4-carboxylate Structure

145451-90-7

methyl (2R,4R)-...

~%

(3R,4S)-(-)-1-BENZYL-3,4-PYRROLIDINDIOL Structure

145451-97-4

(3R,4S)-(-)-1-B...

(4R,5S)-N-Benzyl-4-(t-butyldimethylsilyloxymethyl)-4-hydroxymethyl-5-isopropyloxazoladine Structure

145452-01-3

(4R,5S)-N-Benzy...

~%

(3R,4S)-(-)-1-BENZYL-3,4-PYRROLIDINDIOL Structure

145451-97-4

(3R,4S)-(-)-1-B...

methyl (4R,5S)-3-benzyl-4-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-propan-2-yl-1,3-oxazolidine-4-carboxylate Structure

145451-93-0

methyl (4R,5S)-...

~%

(3R,4S)-(-)-1-BENZYL-3,4-PYRROLIDINDIOL Structure

145451-97-4

(3R,4S)-(-)-1-B...

tert-Butyldimethylsilyl chloride Structure

18162-48-6

tert-Butyldimet...

~%

methyl (4R,5S)-3-benzyl-4-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-propan-2-yl-1,3-oxazolidine-4-carboxylate Structure

145451-93-0

methyl (4R,5S)-...

methyl (2R,4R)-3-benzyl-2-tert-butyl-4-[(1S)-1-hydroxy-2-methylpropyl]-1,3-oxazolidine-4-carboxylate Structure

145451-90-7

methyl (2R,4R)-...

~%

methyl (4R,5S)-3-benzyl-4-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-propan-2-yl-1,3-oxazolidine-4-carboxylate Structure

145451-93-0

methyl (4R,5S)-...

METHYL (2R,3S)-2-BENZYLAMINO-3-HYDROXY-2-HYDROXYMETHYL-4-METHYLPENTANOATE Structure

145451-91-8

METHYL (2R,3S)-...

~%

methyl (4R,5S)-3-benzyl-4-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-propan-2-yl-1,3-oxazolidine-4-carboxylate Structure

145451-93-0

methyl (4R,5S)-...


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