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

Total synthesis of ionomycin using ring-opening strategies

M Lautens, JT Colucci, S Hiebert, ND Smith…

Index: Organic Letters, , vol. 4, # 11 p. 1879 - 1882

Full Text: HTML

Citation Number: 110

Abstract

... Volume: Page: ... Organic Letters. ... S)-BINAP, toluene, 65 °C, 1.1 equiv of DIBAL-H (added over 20 h); (B) (a) DMSO, (COCl) 2 , NEt 3 , CH 2 Cl 2 , −78 °C; (b) PhMe, DIBAL-H, −78 °C; (c) THF, KHMDS, PMBCl; (C) O 3 , MeOH/CH 2 Cl 2 , −78 °C then NaBH 4 , rt; (D ...

3-Pentanone Structure

~82%

2-Chloropentan-3-one Structure

2-Chloropentan-3-one

[4R,6S,8S]-4,6,8-trimethyl-9-oxo-decanoic acid methyl ester Structure

[4R,6S,8S]-4,6,...

~%

Ionomycin Structure

benzoic acid 3-hydroxy-1-[5'-(1-hydroxy-ethyl)-2,5'-dimethyl-octahydro-[2,2']bifuranyl-5-yl-methyl]-20-methoxycarbonyl-2,4,8,10,14,16,18-heptamethyl-11,13-dioxo-eicos-5-enyl ester Structure

benzoic acid 3-...

~%

Ionomycin Structure

N/A Structure

~%

Ionomycin Structure

benzoic acid 3-hydroxy-1-[5'-(1-hydroxy-ethyl)-2,5'-dimethyl-octahydro-[2,2']bifuranyl-5-yl-methyl]-20-methoxycarbonyl-2,4,8,10,14,16,18-heptamethyl-11,13-dioxo-eicos-5-enyl ester Structure

benzoic acid 3-...

~%

Ionomycin Structure

[2R,3S,6E]-toluene-4-sulfonic acid-9-benzenesulfonyl-2-(t-butyldimethylsiloxy)-3-hydroxy-3,7-dimethyl-non-6-enyl ester Structure

[2R,3S,6E]-tolu...

~%

Ionomycin Structure

acetic acid geranyl ester Structure

acetic acid ger...

~%

Ionomycin Structure

acetic acid,8-bromo-3,7-dimethylocta-2,6-dien-1-ol Structure

acetic acid,8-b...

~%

Ionomycin Structure

(E,E)-8-acetoxy-2,6-dimethyl-2,6-octadien-1-ol Structure

(E,E)-8-acetoxy...

~%

Ionomycin Structure

methyl (4R,6S,8S)-9-hydroxy-4,6,8-trimethylnonanoate Structure

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

~%

Ionomycin Structure

N/A Structure

~%

Ionomycin Structure

[4R,6S,6(4S,5R)]-4-methyl-6-(5-methyl-2-thioxo-[1,3]dioxan-4-yl)-heptanoic acid methyl ester Structure

[4R,6S,6(4S,5R)...

~%

Ionomycin Structure

[2S,4S,4(4S,5R)]-4-[5-methyl-2-(4-methoxyphenyl)-[1,3]dioxan-4-yl]-2-methyl-pentan-1-ol Structure

[2S,4S,4(4S,5R)...

~%

Ionomycin Structure

[2R,3R,4S,4(4R,5R)]-4-[5-methyl-2-(4-methoxyphenyl)-[1,3]dioxan-4-yl]-2-methyl-pentan-1,3-diol Structure

[2R,3R,4S,4(4R,...

~%

Ionomycin Structure

N/A Structure

~%

Ionomycin Structure

[4S,6S,6(4S,5R)]-6-[2-(4-methoxyphenyl)-5-methyl-[1,3]dioxan-4-yl]-4-methyl-hept-2-enoic acid methyl ester Structure

[4S,6S,6(4S,5R)...

~%

Ionomycin Structure

[2R,3R,4R,5R,6R]-2,4,6-trimethyl-5-(4-methoxybenzyloxy)-3-((t-butyldimethylsilyl)oxy)-heptane-1,7-diol Structure

[2R,3R,4R,5R,6R...

~%

Ionomycin Structure

[2R,3R,4S,5S]-3-((triisopropylsilyl)oxy)-5-(4-methoxy-benzyloxy)-2,4-dimethylheptane-1,7-diol Structure

[2R,3R,4S,5S]-3...

~%

Ionomycin Structure

N/A Structure

~%

Ionomycin Structure

[2S,2(2R),5R,5(1S)]-5-[3-benzenesulfonyl-1-(trimethylsilyloxy)-1-methyl-propyl]-2-(1-(t-butyldimethylsiloxy)-ethyl)-2-methyl-tetrahydrofuran Structure

[2S,2(2R),5R,5(...

~%

Ionomycin Structure

[3S,4S,5R,6R]-5-((trisopropylsilyl)oxy)-3-(4-methoxy-benzyloxy)-4,6-dimethyl-7-(triphenylmethyl)oxy-heptanal Structure

[3S,4S,5R,6R]-5...

~%

Ionomycin Structure

N/A Structure

~%

Ionomycin Structure

N/A Structure

~%

Ionomycin Structure

N/A Structure

~%

Ionomycin Structure

[2S,2(2R,5S,5(1R)),7S,8S,9R,10R]-7-hydroxy-9-triisopropylsilyloxy-8,10-dimethyl-2-[5-methyl-5-(1-(t-butyldimethylsilyloxy)-ethyl)tetrahydrofuran-2-yl]-2-trimethylsilyloxy-11-trityloxy-undecan-5-one Structure

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

~%

Ionomycin Structure

N/A Structure

~%

Ionomycin Structure

N/A Structure

~%

Ionomycin Structure

Structure

~%

Ionomycin Structure

Structure

~%

Ionomycin Structure

[3S,5R]-6-(4-methoxy-benzyloxy)-3,5-dimethyl-hexanal Structure

[3S,5R]-6-(4-me...

~%

Ionomycin Structure

[3S,5R]-6-(4-methoxy-benzyloxy)-3,5-dimethyl-hexanenitrile Structure

[3S,5R]-6-(4-me...

~%

Ionomycin Structure

[3S,5R]-6-(4-methoxy-benzyloxy)-3,5-dimethyl-hexan-1-ol Structure

[3S,5R]-6-(4-me...

~%

Ionomycin Structure

[2S,4R]-O-(4-toluene-sulfonate)-5-(4-methoxy-benzyloxy)-2,4-dimethyl-pentan-1-ol Structure

[2S,4R]-O-(4-to...

~%

Ionomycin Structure

[3S,5R]-S-(1-phenyl-1H-tetrazol-5-yl)-6-(4-methoxy-benzyloxy)-3,5-dimethyl-hexan-1-thiol Structure

[3S,5R]-S-(1-ph...

~%

Ionomycin Structure

2,4-dimethyl-pentanedioic acid monomethyl ester Structure

2,4-dimethyl-pe...

~%

Ionomycin Structure

[2R,4S]-2,4-dimethyl-pentanedioic acid monomethyl ester Structure

[2R,4S]-2,4-dim...

~%

Ionomycin Structure

[2R,4S]-5-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethyl-pentanoic acid methyl ester Structure

[2R,4S]-5-(tert...

~%

Ionomycin Structure

[2R,4S]-5-hydroxy-2,4-dimethyl-pentanoic acid methyl ester Structure

[2R,4S]-5-hydro...

~%

Ionomycin Structure

N/A Structure

~%

Ionomycin Structure

N/A Structure

~%

Ionomycin Structure

[2R,4S]-5-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethyl-pentan-1-ol Structure

[2R,4S]-5-(tert...

~%

Ionomycin Structure

[4R,6S,8S]-4,6,8-trimethyl-9-oxo-nonanoic acid methyl ester Structure

[4R,6S,8S]-4,6,...

~%

Ionomycin Structure

(2S,3S,4R,5R,9R,11R,E)-1-((2S,2'R,5S,5'S)-5'-((R)-1-((tert-butyldimethylsilyl)oxy)ethyl)-2,5'-dimethyloctahydro-[2,2'-bifuran]-5-yl)-3,5,9,11-tetramethyl-12-oxo-4-((triisopropylsilyl)oxy)dodec-6-en-2-yl benzoate Structure

(2S,3S,4R,5R,9R...

~%

Ionomycin Structure

Products and Mechanism of the Reaction of Chlorine Atoms wit...

[Journal of Physical Chemistry A, , vol. 114, # 1 p. 343 - 354]

Products and Mechanism of the Reaction of Chlorine Atoms wit...

[Journal of Physical Chemistry A, , vol. 114, # 1 p. 343 - 354]

Products and Mechanism of the Reaction of Chlorine Atoms wit...

[Journal of Physical Chemistry A, , vol. 114, # 1 p. 343 - 354]

Products and Mechanism of the Reaction of Chlorine Atoms wit...

[Journal of Physical Chemistry A, , vol. 114, # 1 p. 343 - 354]

Synthesis of [alpha]-Diazoketone by the Action of Diazoalkan...

[Asian Journal of Chemistry, , vol. 22, # 4 p. 2939 - 2942]