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

Total synthesis of ouabagenin and ouabain

…, S Phoenix, P Deslongchamps

Index: Reddy, Maddi Sridhar; Zhang, Hongxing; Phoenix, Serge; Deslongchamps, Pierre Chemistry - An Asian Journal, 2009 , vol. 4, # 5 p. 725 - 741

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Citation Number: 24

Abstract

Abstract All done! A full account of the total synthesis of ouabagenin and ouabain has been described. The synthesis was achieved through a polyanionic cyclization strategy. Degradation studies provide an ultimate proof for a key intermediate observed in the synthesis.

(1R,3R,5R,8R,9S,10S,11R,13R,14S,17S)-17-(((tert-butyldiphenylsilyl)oxy)methyl)-3-(dimethyl(phenyl)silyl)-1,11,14-trihydroxy-10-(((4-methoxybenzyl)oxy)methyl)-13-methylhexadecahydro-7H-cyclopenta[a]phenanthren-7-one Structure

(1R,3R,5R,8R,9S...

~%

4-((3R,3aR,5R,5bR,9aR,11S,12aS,14bS)-5,11,12a,14b-tetrahydroxy-3a,8,8-trimethylhexadecahydro-1H-cyclopenta[7,8]phenanthro[4,4a-d][1,3]dioxin-3-yl)furan-2(5H)-one Structure

4-((3R,3aR,5R,5...

Structure

~%

4-((3R,3aR,5R,5bR,9aR,11S,12aS,14bS)-5,11,12a,14b-tetrahydroxy-3a,8,8-trimethylhexadecahydro-1H-cyclopenta[7,8]phenanthro[4,4a-d][1,3]dioxin-3-yl)furan-2(5H)-one Structure

4-((3R,3aR,5R,5...

(3R,5R,8R,9S,10S,11R,13R,14S,17S)-17-(((tert-butyldiphenylsilyl)oxy)methyl)-3-(dimethyl(phenyl)silyl)-11,14-dihydroxy-10-(((4-methoxybenzyl)oxy)methyl)-13-methyltetradecahydro-1H-cyclopenta[a]phenanthrene-1,7(2H)-dione Structure

(3R,5R,8R,9S,10...

~%

4-((3R,3aR,5R,5bR,9aR,11S,12aS,14bS)-5,11,12a,14b-tetrahydroxy-3a,8,8-trimethylhexadecahydro-1H-cyclopenta[7,8]phenanthro[4,4a-d][1,3]dioxin-3-yl)furan-2(5H)-one Structure

4-((3R,3aR,5R,5...

Structure

~%

4-((3R,3aR,5R,5bR,9aR,11S,12aS,14bS)-5,11,12a,14b-tetrahydroxy-3a,8,8-trimethylhexadecahydro-1H-cyclopenta[7,8]phenanthro[4,4a-d][1,3]dioxin-3-yl)furan-2(5H)-one Structure

4-((3R,3aR,5R,5...

(3R,5R,8R,9S,10S,11R,13R,14S,17S)-17-(((tert-butyldiphenylsilyl)oxy)methyl)-3-(dimethyl(phenyl)silyl)-11,14-dihydroxy-10-(((4-methoxybenzyl)oxy)methyl)-13-methyltetradecahydro-1H-cyclopenta[a]phenanthrene-1,7(2H)-dione Structure

(3R,5R,8R,9S,10...

~%

(1R,3S,5S,8R,9S,10R,11R,13R,14S,17S)-10-(acetoxymethyl)-17-((S)-1,2-dihydroxyethyl)-5,14-dihydroxy-1-((4-methoxybenzoyl)oxy)-13-methylhexadecahydro-1H-cyclopenta[a]phenanthrene-3,11-diyl diacetate Structure

(1R,3S,5S,8R,9S...

(1R,3R,5R,8R,9S,10S,11R,13R,14S,17S)-17-(((tert-butyldiphenylsilyl)oxy)methyl)-3-(dimethyl(phenyl)silyl)-1,11,14-trihydroxy-10-(((4-methoxybenzyl)oxy)methyl)-13-methylhexadecahydro-7H-cyclopenta[a]phenanthren-7-one Structure

(1R,3R,5R,8R,9S...

~%

(1R,3S,5S,8R,9S,10R,11R,13R,14S,17S)-10-(acetoxymethyl)-17-((S)-1,2-dihydroxyethyl)-5,14-dihydroxy-1-((4-methoxybenzoyl)oxy)-13-methylhexadecahydro-1H-cyclopenta[a]phenanthrene-3,11-diyl diacetate Structure

(1R,3S,5S,8R,9S...

Structure

~%

(1R,3S,5S,8R,9S,10R,11R,13R,14S,17S)-10-(acetoxymethyl)-17-((S)-1,2-dihydroxyethyl)-5,14-dihydroxy-1-((4-methoxybenzoyl)oxy)-13-methylhexadecahydro-1H-cyclopenta[a]phenanthrene-3,11-diyl diacetate Structure

(1R,3S,5S,8R,9S...

Structure

~%

(1R,3S,5S,8R,9S,10R,11R,13R,14S,17S)-10-(acetoxymethyl)-17-((S)-1,2-dihydroxyethyl)-5,14-dihydroxy-1-((4-methoxybenzoyl)oxy)-13-methylhexadecahydro-1H-cyclopenta[a]phenanthrene-3,11-diyl diacetate Structure

(1R,3S,5S,8R,9S...

(3R,5R,8R,9S,10S,11R,13R,14S,17S)-17-(((tert-butyldiphenylsilyl)oxy)methyl)-3-(dimethyl(phenyl)silyl)-11,14-dihydroxy-10-(((4-methoxybenzyl)oxy)methyl)-13-methyltetradecahydro-1H-cyclopenta[a]phenanthrene-1,7(2H)-dione Structure

(3R,5R,8R,9S,10...

~%

Structure

(1R,3R,5R,8R,9S,10S,11R,13R,14S,17S)-17-(((tert-butyldiphenylsilyl)oxy)methyl)-3-(dimethyl(phenyl)silyl)-1,11,14-trihydroxy-10-(((4-methoxybenzyl)oxy)methyl)-13-methylhexadecahydro-7H-cyclopenta[a]phenanthren-7-one Structure

(1R,3R,5R,8R,9S...

~%

Structure

(3R,5R,8R,9S,10S,11R,13R,14S,17S)-17-(((tert-butyldiphenylsilyl)oxy)methyl)-3-(dimethyl(phenyl)silyl)-11,14-dihydroxy-10-(((4-methoxybenzyl)oxy)methyl)-13-methyltetradecahydro-1H-cyclopenta[a]phenanthrene-1,7(2H)-dione Structure

(3R,5R,8R,9S,10...

~%

(1R,3S,5S,8R,9S,10R,11R,13R,14S,17S)-10-(acetoxymethyl)-3-(dimethyl(phenyl)silyl)-5,11,14-trihydroxy-17-(hydroxymethyl)-13-methylhexadecahydro-1H-cyclopenta[a]phenanthren-1-yl 4-methoxybenzoate Structure

(1R,3S,5S,8R,9S...

(1R,3R,5R,8R,9S,10S,11R,13R,14S,17S)-17-(((tert-butyldiphenylsilyl)oxy)methyl)-3-(dimethyl(phenyl)silyl)-1,11,14-trihydroxy-10-(((4-methoxybenzyl)oxy)methyl)-13-methylhexadecahydro-7H-cyclopenta[a]phenanthren-7-one Structure

(1R,3R,5R,8R,9S...

~%

(1R,3S,5S,8R,9S,10R,11R,13R,14S,17S)-10-(acetoxymethyl)-3-(dimethyl(phenyl)silyl)-5,11,14-trihydroxy-17-(hydroxymethyl)-13-methylhexadecahydro-1H-cyclopenta[a]phenanthren-1-yl 4-methoxybenzoate Structure

(1R,3S,5S,8R,9S...

Structure

~%

(1R,3S,5S,8R,9S,10R,11R,13R,14S,17S)-10-(acetoxymethyl)-3-(dimethyl(phenyl)silyl)-5,11,14-trihydroxy-17-(hydroxymethyl)-13-methylhexadecahydro-1H-cyclopenta[a]phenanthren-1-yl 4-methoxybenzoate Structure

(1R,3S,5S,8R,9S...

Structure

~%

(1R,3S,5S,8R,9S,10R,11R,13R,14S,17S)-10-(acetoxymethyl)-3-(dimethyl(phenyl)silyl)-5,11,14-trihydroxy-17-(hydroxymethyl)-13-methylhexadecahydro-1H-cyclopenta[a]phenanthren-1-yl 4-methoxybenzoate Structure

(1R,3S,5S,8R,9S...

(3R,5R,8R,9S,10S,11R,13R,14S,17S)-17-(((tert-butyldiphenylsilyl)oxy)methyl)-3-(dimethyl(phenyl)silyl)-11,14-dihydroxy-10-(((4-methoxybenzyl)oxy)methyl)-13-methyltetradecahydro-1H-cyclopenta[a]phenanthrene-1,7(2H)-dione Structure

(3R,5R,8R,9S,10...

~%

Structure

(1R,3R,5R,8R,9S,10S,11R,13R,14S,17S)-17-(((tert-butyldiphenylsilyl)oxy)methyl)-3-(dimethyl(phenyl)silyl)-1,11,14-trihydroxy-10-(((4-methoxybenzyl)oxy)methyl)-13-methylhexadecahydro-7H-cyclopenta[a]phenanthren-7-one Structure

(1R,3R,5R,8R,9S...

~%

Structure