Tetrahedron letters

Synthesis of oleandomycin through the intact aglycone, oleandolide

K Tatsuta, Y Kobayashi, H Gunji, H Masuda

Index: Tatsuta; Kobayashi; Gunji; Masuda Tetrahedron Letters, 1988 , vol. 29, # 32 p. 3975 - 3978

Full Text: HTML

Citation Number: 32

Abstract

Download full text in PDF Opens in a new window. Article suggestions will be shown in a dialog on return to ScienceDirect. ... Please enable JavaScript to use all the features on this page. ... Oleandomycin has been reconstructed by an introduction of the two sugar units onto the intact aglycone, oleandolide, which was first synthesized through the stereoselective oxidation of the 8-exo-methylene derivative. ... Oleandomycin( ) was led to oleandolide ( ) through the ...

 Related Synthetic Route
Oleandomycin Structure

3922-90-5

Oleandomycin

~44%

6-[4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-8,14-dihydroxy-5,7,9,12,13,15-hexamethyl-1,11-dioxaspiro[2.13]hexadecane-10,16-dione Structure

4166-78-3

6-[4-(dimethyla...

(2S,3R,4S,6R)-2-(((3R,5R,6S,7R,8R,11R,12S,13S,14S,15S)-6,12-dihydroxy-5,7,8,11,13,15-hexamethyl-4,10-dioxo-1,9-dioxaspiro[2.13]hexadecan-14-yl)oxy)-4-(dimethylamino)-6-methyltetrahydro-2H-pyran-3-yl acetate Structure

119870-73-4

(2S,3R,4S,6R)-2...

~91%

6-[4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-8,14-dihydroxy-5,7,9,12,13,15-hexamethyl-1,11-dioxaspiro[2.13]hexadecane-10,16-dione Structure

4166-78-3

6-[4-(dimethyla...

(1S,2R,2'R,5R,6R,7R,8R,9R,12S,13S,17R)-15-(4-bromophenyl)-7,9-dihydroxy-2,5,6,8,12,17-hexamethyl-4,14,16-trioxaspiro[bicyclo[11.3.1]heptadecane-10,2'-oxiran]-3-one Structure

119870-69-8

(1S,2R,2'R,5R,6...

~%

6-[4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-8,14-dihydroxy-5,7,9,12,13,15-hexamethyl-1,11-dioxaspiro[2.13]hexadecane-10,16-dione Structure

4166-78-3

6-[4-(dimethyla...

(1S,2R,5R,6R,7R,8R,9R,12S,13S,17R)-15-(4-bromophenyl)-7,9-dihydroxy-2,5,6,8,12,17-hexamethyl-10-methylene-4,14,16-trioxabicyclo[11.3.1]heptadecan-3-one Structure

119887-69-3

(1S,2R,5R,6R,7R...

~%

6-[4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-8,14-dihydroxy-5,7,9,12,13,15-hexamethyl-1,11-dioxaspiro[2.13]hexadecane-10,16-dione Structure

4166-78-3

6-[4-(dimethyla...

(1S,2R,2'R,5R,6R,7S,8R,12S,13S,17R)-15-(4-bromophenyl)-7-hydroxy-2,5,6,8,12,17-hexamethyl-4,14,16-trioxaspiro[bicyclo[11.3.1]heptadecane-10,2'-oxirane]-3,9-dione Structure

119870-70-1

(1S,2R,2'R,5R,6...

~%

6-[4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-8,14-dihydroxy-5,7,9,12,13,15-hexamethyl-1,11-dioxaspiro[2.13]hexadecane-10,16-dione Structure

4166-78-3

6-[4-(dimethyla...

oleandolide Structure

68540-16-9

oleandolide

~%

6-[4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-8,14-dihydroxy-5,7,9,12,13,15-hexamethyl-1,11-dioxaspiro[2.13]hexadecane-10,16-dione Structure

4166-78-3

6-[4-(dimethyla...

(2S,3R,4S,6R)-4-(dimethylamino)-6-methyl-2-(pyrimidin-2-ylthio)tetrahydro-2H-pyran-3-yl acetate Structure

119870-72-3

(2S,3R,4S,6R)-4...

~%

6-[4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-8,14-dihydroxy-5,7,9,12,13,15-hexamethyl-1,11-dioxaspiro[2.13]hexadecane-10,16-dione Structure

4166-78-3

6-[4-(dimethyla...

(1S,2R,2'R,5R,6R,7R,8R,9R,12S,13S,17R)-15-(4-bromophenyl)-7,9-dihydroxy-2,5,6,8,12,17-hexamethyl-4,14,16-trioxaspiro[bicyclo[11.3.1]heptadecane-10,2'-oxiran]-3-one Structure

119870-69-8

(1S,2R,2'R,5R,6...

~%

Oleandomycin Structure

3922-90-5

Oleandomycin

(1S,2R,5R,6R,7R,8R,9R,12S,13S,17R)-15-(4-bromophenyl)-7,9-dihydroxy-2,5,6,8,12,17-hexamethyl-10-methylene-4,14,16-trioxabicyclo[11.3.1]heptadecan-3-one Structure

119887-69-3

(1S,2R,5R,6R,7R...

~%

Oleandomycin Structure

3922-90-5

Oleandomycin

(1S,2R,2'R,5R,6R,7S,8R,12S,13S,17R)-15-(4-bromophenyl)-7-hydroxy-2,5,6,8,12,17-hexamethyl-4,14,16-trioxaspiro[bicyclo[11.3.1]heptadecane-10,2'-oxirane]-3,9-dione Structure

119870-70-1

(1S,2R,2'R,5R,6...

~%

Oleandomycin Structure

3922-90-5

Oleandomycin

oleandolide Structure

68540-16-9

oleandolide

~%

Oleandomycin Structure

3922-90-5

Oleandomycin

(2S,3R,4S,6R)-4-(dimethylamino)-6-methyl-2-(pyrimidin-2-ylthio)tetrahydro-2H-pyran-3-yl acetate Structure

119870-72-3

(2S,3R,4S,6R)-4...

~%

Oleandomycin Structure

3922-90-5

Oleandomycin

methyl 2,6-dideoxy-3-O-methyl-α-D-ribo-hexopyranoside Structure

4166-79-4

methyl 2,6-dide...

~%

Oleandomycin Structure

3922-90-5

Oleandomycin

benzyl ((2S,3S,4S)-4-methoxy-2-methyl-3,4-dihydro-2H-pyran-3-yl) carbonate Structure

120308-65-8

benzyl ((2S,3S,...

(2S,3R,4S,6R)-2-(((3R,5R,6S,7R,8R,11R,12S,13S,14S,15S)-6,12-dihydroxy-5,7,8,11,13,15-hexamethyl-4,10-dioxo-1,9-dioxaspiro[2.13]hexadecan-14-yl)oxy)-4-(dimethylamino)-6-methyltetrahydro-2H-pyran-3-yl acetate Structure

119870-73-4

(2S,3R,4S,6R)-2...

~%

Oleandomycin Structure

3922-90-5

Oleandomycin


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