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

Diastereo??and Enantioselective Total Synthesis of Stigmatellin A

D Enders, G Geibel, S Osborne

Index: Enders, Dieter; Geibel, Gunter; Osborne, Simon Chemistry - A European Journal, 2000 , vol. 6, # 8 p. 1302 - 1309

Full Text: HTML

Citation Number: 39

Abstract

Abstract Stigmatellin A (1) isolated from the myxobacterium Stigmatella aurantiaca is a powerful inhibitor of electron transport in mitochondria and chloroplasts. The first highly diastereo-and enantioselective total synthesis of this important natural product is described. Key steps in the synthesis are the alkylation of the SAMP-hydrazone (S)-13, a titanium mediated syn-diastereoselective aldol reaction, the anti-diastereoselective ...

[(2E,4E)-4-Methyl-2,4-hexadienyl]phosphonic Acid Diethyl Ester Structure

[(2E,4E)-4-Meth...

(2R,3S,4S,5S)-7-[8-hydroxy-5,7-dimethoxy-3-methyl-4-oxo-4H-2-chromenyl]-2,4-dimethoxy-3,5-dimethylheptanal Structure

(2R,3S,4S,5S)-7...

~76%

STIGMATELLIN Structure

1-(2,3-Dihydroxy-4,6-dimethoxyphenyl)-1-propanone Structure

1-(2,3-Dihydrox...

~%

STIGMATELLIN Structure

3,5-Dimethoxyphenol Structure

3,5-Dimethoxyphenol

~%

STIGMATELLIN Structure

1-[2-Hydroxy-4,6-dimethoxy-3-(1-oxopropoxy)phenyl]-1-propanone Structure

1-[2-Hydroxy-4,...

~%

STIGMATELLIN Structure

1-[2-Hydroxy-4,6-dimethoxy-3-(MethoxyMethoxy)phenyl]-1-propanone Structure

1-[2-Hydroxy-4,...

~%

STIGMATELLIN Structure

(4S,5S,6S,7R)-5,7-Dimethoxy-4,6-dimethyl-8-(phenylmethoxy)-1-octanol Structure

(4S,5S,6S,7R)-5...

~%

STIGMATELLIN Structure

(4S,5S,6S,7R)-5,7-Dimethoxy-4,6-dimethyl-8-(phenylmethoxy)-octanoic Acid Structure

(4S,5S,6S,7R)-5...

~%

STIGMATELLIN Structure

(2R,3S,4S,5S)-(+)-1-Benzyloxy-2,4-dimethoxy-8-(4'-methoxyphenoxy)-3,5-dimethyloctane Structure

(2R,3S,4S,5S)-(...

~%

STIGMATELLIN Structure

(4S,5S,6S,7R)-8-Benzyloxy-5,7-dimethoxy-4,6-dimethyloctanoic acid 3,5-dimethoxy-2-methoxymethoxy-6-propionylphenyl ester Structure

(4S,5S,6S,7R)-8...

~%

STIGMATELLIN Structure

2-[(3S,4S,5S,6R)-7-Benzyloxy-4,6-dimethylheptyl]-5,7-dimethoxy-8-methoxymethoxy-3-methyl-4H-1-benzopyran-4-one Structure

2-[(3S,4S,5S,6R...

~%

STIGMATELLIN Structure

trans-2-Methyl-2-butenal Structure

trans-2-Methyl-...

~%

STIGMATELLIN Structure

(2E,4E)-4-methyl-2,4-hexadien-1-ol Structure

(2E,4E)-4-methy...

~%

STIGMATELLIN Structure

(2E,4E)-1-Bromo-4-methylhexa-2,4-diene Structure

(2E,4E)-1-Bromo...

~%

STIGMATELLIN Structure

2-[(3S,4S,5S,6R)-7-Hydroxy-4,6-dimethoxy-3,5-dimethylheptyl]-5,7-dimethoxy-8-(MethoxyMethoxy)-3-Methyl-2,3-dihydro-4H-1-benzopyran-4-one Structure

2-[(3S,4S,5S,6R...

~%

STIGMATELLIN Structure

3-Chloropropyl 4-Methoxyphenyl Ether Structure

3-Chloropropyl ...

~84%

3-(4-METHOXYPHENOXY)-1-IODOPROPANE Structure

3-(4-METHOXYPHE...