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

Total synthesis of the polyether antibiotic ionomycin

DA Evans, RL Dow, TL Shih, JM Takacs…

Index: Journal of the American Chemical Society, , vol. 112, # 13 p. 5290 - 5313

Full Text: HTML

Citation Number: 231

Abstract

... Professor D. A. Evans for providing us with spectroscopic data and other information on compound ... James M. Takacs, and Robert Zahler Contribution from the Department of Chemistry, Harvard Uniuersity. ... 0002-7863/90/ 15 12-5290$02.50/0 0 1990 American Chemical Society ...

(S)-3-((R)-3-(benzyloxy)-2-methylpropanoyl)-4-isopropyloxazolidin-2-one Structure

(S)-3-((R)-3-(b...

~%

(S)-4-Isopropyl-3-propionyl-2-oxazolidinone Structure

(S)-4-Isopropyl...

(S)-3-((R)-3-(benzyloxy)-2-methylpropanoyl)-4-isopropyloxazolidin-2-one Structure

(S)-3-((R)-3-(b...

~0%

(-)-(S)-1-benzyloxy-3-hydroxy-2-methylpropane Structure

(-)-(S)-1-benzy...

(S)-4-Isopropyl-2-oxazolidinone Structure

(S)-4-Isopropyl...

ionomycin methyl ester Structure

ionomycin methy...

~%

Ionomycin Structure

N/A Structure

~%

Ionomycin Structure

(3R,4S)-1-(benzyloxy)-3-hydroxy-4-(hydroxymethyl)-2-methyl-5-hexene Structure

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

~%

Ionomycin Structure

(1S,2R,6R,4Z)-5-(3'-(benzyloxy)propyl)-1,2,4-trimethyl-3,9-dioxabicyclo[4.2.1]non-4-ene Structure

(1S,2R,6R,4Z)-5...

~%

Ionomycin Structure

(1'R,2R,5S)-5-(1'-acetoxyethyl)-5-methyl-2-(1''-oxo-4''-(benzyloxy)butyl)tetrahydrofuran Structure

(1'R,2R,5S)-5-(...

~%

Ionomycin Structure

(3R,4S)-1-(benzyloxy)-3-hydroxy-2-methyl-4-((((4-methylphenyl)sulfonyl)oxy)methyl)-5-hexene Structure

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

~%

Ionomycin Structure

(S)-4-((tert-butyldimethylsilyl)oxy)-4-((2R,5S)-5-((R)-1-((tert-butyldimethylsilyl)oxy)ethyl)-5-methyltetrahydrofuran-2-yl)pentyl methanesulfonate Structure

(S)-4-((tert-bu...

~%

Ionomycin Structure

N/A Structure

~%

Ionomycin Structure

(1''R,1'R,2R,5S)-5-(1'-(tert-butyldimethylsiloxy)ethyl)-5-methyl-2-(1''-(tert-butyldimethylsiloxy)-1''-methyl-4''-(benzyloxy)butyl)tetrahydrofuran Structure

(1''R,1'R,2R,5S...

~%

Ionomycin Structure

N/A Structure

~%

Ionomycin Structure

(2R,3R,4S)-1-(benzyloxy)-2,4-dimethyl-6-(diphenyl-tert-butylsiloxy)-2,4-hexanediol Structure

(2R,3R,4S)-1-(b...

~%

Ionomycin Structure

(1'R,4R,5S)-4-(2'-(benzyloxy)-1'-methylethyl)-6-((diphenyl-tert-butylsiloxy)methyl)-2,2,5-trimethyl-1,3-dioxane Structure

(1'R,4R,5S)-4-(...

~%

Ionomycin Structure

((R)-1-((2R,2'S,5S,5'S)-5'-(((4S,5S,6R)-6-((R)-1-(benzyloxy)propan-2-yl)-2,2,5-trimethyl-1,3-dioxan-4-yl)methyl)-2',5-dimethyloctahydro-[2,2'-bifuran]-5-yl)ethoxy)(tert-butyl)dimethylsilane Structure

((R)-1-((2R,2'S...

~%

Ionomycin Structure

N/A Structure

~%

Ionomycin Structure

((S)-4-((tert-butyldimethylsilyl)oxy)-4-((2R,5S)-5-((R)-1-((tert-butyldimethylsilyl)oxy)ethyl)-5-methyltetrahydrofuran-2-yl)pentyl)triphenylphosphonium iodide Structure

((S)-4-((tert-b...

~%

Ionomycin Structure

(2R,3R,4S)-1-(benzyloxy)-2,4-dimethyl-3-hydroxy-5-hexene Structure

(2R,3R,4S)-1-(b...

~%

Ionomycin Structure

(1'R,4R,5S,6R)-4-(2'-(benzyloxy)-1'-methylethyl)-6-(hydroxymethyl)-2,2,5-trimethyl-1,3-dioxane Structure

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

~%

Ionomycin Structure

(1''S,1'R,2R,5S)-5-(1'-hydroxyethyl)-5-methyl-2-(1''-hydroxy-1''-methyl-4''-(benzyloxy)butyl)tetrahydrofuran Structure

(1''S,1'R,2R,5S...

~%

Ionomycin Structure

N/A Structure

~%

Ionomycin Structure

(+)-(4S)-3-(5-(benzyloxy)-(2S)-((2R,5S)-5-methyl-5-((1R)-1-hydroxyethyl)tetrahydrofuranyl)pentanoyl)-4-isopropyl-1,3-oxazolidin-2-one Structure

(+)-(4S)-3-(5-(...

~%

Ionomycin Structure

(2S,3S)-3-((1,1-dimethylethyl)dimethylsiloxy)-2-methyl-1-butanol Structure

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

~%

Ionomycin Structure

(2R,3S)-3-(tert-butyldimethylsilyloxy)-2-methylbutanal Structure

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

~%

Ionomycin Structure

N/A Structure

~%

Ionomycin Structure

(2E,4S,5S)-5-((1,1-dimethylethyl)dimethylsiloxy)-2,4-dimethyl-2-hexen-2-ol Structure

(2E,4S,5S)-5-((...

~%

Ionomycin Structure

(4S,5S)-5-((1,1-dimethylethyl)dimethylsiloxy)-2,4-dimethyl-1-iodo-2-hexene Structure

(4S,5S)-5-((1,1...

~%

Ionomycin Structure

(2S,6S,7S)-7-((1,1-dimethylethyl)dimethylsiloxy)-2,4,6-trimethyl-4-octen-1-ol Structure

(2S,6S,7S)-7-((...

~%

Ionomycin Structure

(4S,8S,9S)-9-hydroxy-4,6,8-trimethyl-2,6-decadienoic acid methyl ester Structure

(4S,8S,9S)-9-hy...

~%

Ionomycin Structure

(4R,6E)-2,4-dimethyl-7-phenyl-6-heptenoic acid Structure

(4R,6E)-2,4-dim...

~%

Ionomycin Structure

(4S,5S)-5-((1,1-dimethylethyl)dimethylsiloxy)-2,4-dimethyl-2-hexenoic acid ethyl ester Structure

(4S,5S)-5-((1,1...

~%

Ionomycin Structure

N/A Structure

~%

Ionomycin Structure

(4S,8S,9S)-9-((1,1-dimethylethyl)dimethylsiloxy)-4,6,8-trimethyl-2,6-decadienoic acid methyl ester Structure

(4S,8S,9S)-9-((...

~%

Ionomycin Structure

(2S,4'R,6'E)-1-(2',4'-dimethyl-7'-phenyl-6'-heptenoyl)-2-(hydroxymethyl)pyrrolidine Structure

(2S,4'R,6'E)-1-...

~%

Ionomycin Structure

(4R,5S,2'R,3'S)-5-(2'-methyl-3'-hydroxybutanoyl)-4-methyl-5-phenyl-1,3-oxazolidin-2-one Structure

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

~%

Ionomycin Structure

N/A Structure

~%

Ionomycin Structure

N/A Structure

~%

Ionomycin Structure

tert-butyl(((2R,4S)-2,4-dimethyl-6-(phenylthio)hexyl)oxy)diphenylsilane Structure

tert-butyl(((2R...

~%

Ionomycin Structure

(2'S,4R,5S,6'S,7'S)-3-(7'-((1'',1''-dimethylethyl)dimethylsiloxy)-2',4',6'-trimethyl-4'-octenoyl)-4-methyl-5-phenyl-1,3-oxazolidin-2-one Structure

(2'S,4R,5S,6'S,...

~%

Ionomycin Structure

(2R,4S)-2,4-dimethyl-1-((1,1-dimethylethyl)diphenylsiloxy)-6-(phenylsulfonyl)hexane Structure

(2R,4S)-2,4-dim...

~%

Ionomycin Structure

N/A Structure

~%

Ionomycin Structure

N/A Structure

~%

Ionomycin Structure

methyl (4R,6S,8S,12R,14R,18R,E)-18-((4R,5S,6S)-6-(((2S,2'R,5'S)-5'-((R)-1-((tert-butyldimethylsilyl)oxy)ethyl)-2,5'-dimethyloctahydro-[2,2'-bifuran]-5-yl)methyl)-2,2,5-trimethyl-1,3-dioxan-4-yl)-11-hydroxy-4,6,8,12,14-pentamethyl-9-oxononadec-16-enoate Structure

methyl (4R,6S,8...

~%

Ionomycin Structure

(4R,6S,8S,10Z,12R,14R,16E,18R,19R,20S,21S,22(2S,5S(2R,5S(R))))-4,6,8,12,14,18,20-heptamethyl-11-hydroxy-19,21-((1-methylethylidene)dioxy)-9-oxo-22-(tetrahydro-5-methyl-5-(tetrahydro-5-(1-((1,1-dimethylethyl)dimethylsiloxy)ethyl)-5-methyl-2-furanyl)-2... Structure

(4R,6S,8S,10Z,1...

~%

Ionomycin Structure

N/A Structure

~%

Ionomycin Structure

(3S,5S)-6-(tert-butyldiphenylsilyloxy)-3,5-dimethylhexan-1-ol Structure

(3S,5S)-6-(tert...

~%

Ionomycin Structure

(R)-2-{(4R,5S,6S)-6-[[(2S,2'R,5'S)-5'-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-2,5'-dimethyl-octahydro-2,2'-bifuran-5-yl]methyl]-2,2,5-trimethyl-1,3-dioxan-4-yl}propan-1-ol Structure

(R)-2-{(4R,5S,6...

~%

Ionomycin Structure

(S)-2-{(4S,5S,6S)-6-[[(2S,2'R,5'S)-5'-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-2,5'-dimethyl-octahydro-2,2'-bifuran-5-yl]methyl]-2,2,5-trimethyl-1,3-dioxan-4-yl}propanal Structure

(S)-2-{(4S,5S,6...

~%

Ionomycin Structure

N/A Structure

~%

Ionomycin Structure

(2R,4R,8R,E)-8-((4R,5S,6S)-6-(((2S,2'R,5'S)-5'-((R)-1-((tert-butyldimethylsilyl)oxy)ethyl)-2,5'-dimethyloctahydro-[2,2'-bifuran]-5-yl)methyl)-2,2,5-trimethyl-1,3-dioxan-4-yl)-2,4-dimethylnon-6-enal Structure

(2R,4R,8R,E)-8-...

~%

Ionomycin Structure

Deglycobleomycin A 6 analogues modified in the methylvalerat...

[Cai, Xiaoqing; Zaleski, Paul A.; Cagir, Ali; Hecht, Sidney M. Bioorganic and Medicinal Chemistry, 2011 , vol. 19, # 12 p. 3831 - 3844]

Interaction Modes of Titanium Tetrachloride with the Carbony...

[Chemische Berichte, , vol. 129, # 11 p. 1361 - 1368]

One pot synthesis of N-derivatized 2-oxazolidinones from ami...

[Tetrahedron Letters, , vol. 35, # 51 p. 9533 - 9536]

Chemoselective N??Acylation of Indoles and Oxazolidinones wi...

[Heller, Stephen T.; Schultz, Erica E.; Sarpong, Richmond Angewandte Chemie - International Edition, 2012 , vol. 51, # 33 p. 8304 - 8308]

Absolute Configuration of Lactams and Oxazolidinones Using K...

[Organic Letters, , vol. 15, # 3 p. 472 - 475]