e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

Tetrahedron

Synthesis of trichostatin A, a potent differentiation inducer of Friend leukemic cells, and its antipode

K Mori, K Koseki

Index: Mori, Kenji; Koseki, Koshi Tetrahedron, 1988 , vol. 44, # 19 p. 6013 - 6020

Full Text: HTML

Citation Number: 110

Abstract

This document does not have an outline. ... JavaScript is disabled on your browser. Please enable JavaScript to use all the features on this page. ... Author links open the overlay panel. Numbers correspond to the affiliation list which can be exposed by using the show more link. ... Both the enantiomers of trichostatic acid (1, 98% ee) and trichostatin A (2, 93% ee) were synthesized employing methyl (R)- or (S)-3-hydroxy-2-methyl-propanoate as a starting material.

(R)-trichostatic acid Structure

(R)-trichostati...

~%

Trichostatin A S-isomer Structure

Trichostatin A ...

(2S)-3-(4-(dimethylamino)phenyl)-3-((2-methoxypropan-2-yl)oxy)-2-methylpropanal Structure

(2S)-3-(4-(dime...

~%

Trichostatin A S-isomer Structure

Trichostatin A ...

3-t-butyldimethylsilyloxy-1-(4'-N,N-dimethylaminophenyl)-2-(S)-methyl-1-propanol Structure

3-t-butyldimeth...

~%

(2S)-3-(4-(dimethylamino)phenyl)-3-((2-methoxypropan-2-yl)oxy)-2-methylpropanal Structure

(2S)-3-(4-(dime...

3-t-butyldimethylsilyloxy-1-(4'-N,N-dimethylaminophenyl)-1-(2-methoxypropyloxy)-2-(S)-methylpropane Structure

3-t-butyldimeth...

~%

(2S)-3-(4-(dimethylamino)phenyl)-3-((2-methoxypropan-2-yl)oxy)-2-methylpropanal Structure

(2S)-3-(4-(dime...

(2R)-3-{[tert-butyl(dimethyl)silyl]oxy}-2-methyl-1-propanol Structure

(2R)-3-{[tert-b...

~%

3-t-butyldimethylsilyloxy-1-(4'-N,N-dimethylaminophenyl)-1-(2-methoxypropyloxy)-2-(S)-methylpropane Structure

3-t-butyldimeth...

(2S)-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-methylpropanal Structure

(2S)-3-[[(1,1-d...

~%

3-t-butyldimethylsilyloxy-1-(4'-N,N-dimethylaminophenyl)-1-(2-methoxypropyloxy)-2-(S)-methylpropane Structure

3-t-butyldimeth...

(2R)-3-{[tert-butyl(dimethyl)silyl]oxy}-2-methyl-1-propanol Structure

(2R)-3-{[tert-b...

~%

3-t-butyldimethylsilyloxy-1-(4'-N,N-dimethylaminophenyl)-2-(S)-methyl-1-propanol Structure

3-t-butyldimeth...

methyl 4,6-(R)-dimethyl-7-(4'-N,N-dimethylaminophenyl)-7-(2-methoxypropyloxy)-2,4-heptadienoate Structure

methyl 4,6-(R)-...

~81%

4,6-(R)-dimethyl-7-(4'-N,N-dimethylaminophenyl)-7-hydroxy-2,4-heptadienoic acid Structure

4,6-(R)-dimethy...

3-(4'-N,N-dimethylaminophenyl)-3-(2-methoxypropyloxy)-2-(R)-methyl-1-propanol Structure

3-(4'-N,N-dimet...

~%

4,6-(R)-dimethyl-7-(4'-N,N-dimethylaminophenyl)-7-hydroxy-2,4-heptadienoic acid Structure

4,6-(R)-dimethy...

2,4-(R)-dimethyl-5-(4'-N,N-dimethylaminophenyl)-5-(2-methoxypropyloxy)-2-penten-1-ol Structure

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

~%

4,6-(R)-dimethyl-7-(4'-N,N-dimethylaminophenyl)-7-hydroxy-2,4-heptadienoic acid Structure

4,6-(R)-dimethy...

(4R,5R,E)-5-(4-(dimethylamino)phenyl)-5-((2-methoxypropan-2-yl)oxy)-2,4-dimethylpent-2-enal Structure

(4R,5R,E)-5-(4-...

~%

4,6-(R)-dimethyl-7-(4'-N,N-dimethylaminophenyl)-7-hydroxy-2,4-heptadienoic acid Structure

4,6-(R)-dimethy...

ethyl 2,4-(R)-dimethyl-5-(4'-N,N-dimethylaminophenyl)-5-(2-methoxypropyloxy)-2-pentenoate Structure

ethyl 2,4-(R)-d...

~%

4,6-(R)-dimethyl-7-(4'-N,N-dimethylaminophenyl)-7-hydroxy-2,4-heptadienoic acid Structure

4,6-(R)-dimethy...

(2S)-3-(4-(dimethylamino)phenyl)-3-((2-methoxypropan-2-yl)oxy)-2-methylpropanal Structure

(2S)-3-(4-(dime...

~%

O-(2-methoxypropyl)-(S)-trichostatin A Structure

O-(2-methoxypro...

3-t-butyldimethylsilyloxy-1-(4'-N,N-dimethylaminophenyl)-2-(S)-methyl-1-propanol Structure

3-t-butyldimeth...

~%

O-(2-methoxypropyl)-(S)-trichostatin A Structure

O-(2-methoxypro...

3-t-butyldimethylsilyloxy-1-(4'-N,N-dimethylaminophenyl)-1-(2-methoxypropyloxy)-2-(S)-methylpropane Structure

3-t-butyldimeth...

~%

O-(2-methoxypropyl)-(S)-trichostatin A Structure

O-(2-methoxypro...

3-(4'-N,N-dimethylaminophenyl)-3-(2-methoxypropyloxy)-2-(R)-methyl-1-propanol Structure

3-(4'-N,N-dimet...

~%

methyl 4,6-(R)-dimethyl-7-(4'-N,N-dimethylaminophenyl)-7-(2-methoxypropyloxy)-2,4-heptadienoate Structure

methyl 4,6-(R)-...

2,4-(R)-dimethyl-5-(4'-N,N-dimethylaminophenyl)-5-(2-methoxypropyloxy)-2-penten-1-ol Structure

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

~%

methyl 4,6-(R)-dimethyl-7-(4'-N,N-dimethylaminophenyl)-7-(2-methoxypropyloxy)-2,4-heptadienoate Structure

methyl 4,6-(R)-...

ethyl 2,4-(R)-dimethyl-5-(4'-N,N-dimethylaminophenyl)-5-(2-methoxypropyloxy)-2-pentenoate Structure

ethyl 2,4-(R)-d...

~%

methyl 4,6-(R)-dimethyl-7-(4'-N,N-dimethylaminophenyl)-7-(2-methoxypropyloxy)-2,4-heptadienoate Structure

methyl 4,6-(R)-...

4,6-(R)-dimethyl-7-(4'-N,N-dimethylaminophenyl)-7-hydroxy-2,4-heptadienoic acid Structure

4,6-(R)-dimethy...

~37%

(R)-trichostatic acid Structure

(R)-trichostati...

3-(4'-N,N-dimethylaminophenyl)-3-(2-methoxypropyloxy)-2-(R)-methyl-1-propanol Structure

3-(4'-N,N-dimet...

~%

(4R,5R,E)-5-(4-(dimethylamino)phenyl)-5-((2-methoxypropan-2-yl)oxy)-2,4-dimethylpent-2-enal Structure

(4R,5R,E)-5-(4-...

ethyl 2,4-(R)-dimethyl-5-(4'-N,N-dimethylaminophenyl)-5-(2-methoxypropyloxy)-2-pentenoate Structure

ethyl 2,4-(R)-d...

~%

(4R,5R,E)-5-(4-(dimethylamino)phenyl)-5-((2-methoxypropan-2-yl)oxy)-2,4-dimethylpent-2-enal Structure

(4R,5R,E)-5-(4-...

2,4-(R)-dimethyl-5-(4'-N,N-dimethylaminophenyl)-5-(2-methoxypropyloxy)-2-penten-1-ol Structure

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

~%

(4R,5R,E)-5-(4-(dimethylamino)phenyl)-5-((2-methoxypropan-2-yl)oxy)-2,4-dimethylpent-2-enal Structure

(4R,5R,E)-5-(4-...

ethyl 2,4-(R)-dimethyl-5-(4'-N,N-dimethylaminophenyl)-5-(2-methoxypropyloxy)-2-pentenoate Structure

ethyl 2,4-(R)-d...

~90%

2,4-(R)-dimethyl-5-(4'-N,N-dimethylaminophenyl)-5-(2-methoxypropyloxy)-2-penten-1-ol Structure

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

3-(4'-N,N-dimethylaminophenyl)-3-(2-methoxypropyloxy)-2-(R)-methyl-1-propanol Structure

3-(4'-N,N-dimet...

~%

2,4-(R)-dimethyl-5-(4'-N,N-dimethylaminophenyl)-5-(2-methoxypropyloxy)-2-penten-1-ol Structure

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

3-(4'-N,N-dimethylaminophenyl)-3-(2-methoxypropyloxy)-2-(R)-methyl-1-propanol Structure

3-(4'-N,N-dimet...

~%

ethyl 2,4-(R)-dimethyl-5-(4'-N,N-dimethylaminophenyl)-5-(2-methoxypropyloxy)-2-pentenoate Structure

ethyl 2,4-(R)-d...