Tetrahedron letters

A highly stereocontrolled total synthesis of the polyether antibiotic salinomycin. Crucial role of the 40-metoxybenzyl;(mpm) protecting group for hydroxy functions

K Horita, Y Oikawa, S Nagato, O Yonemitsu

Index: Horita; Oikawa; Nagato; Yonemitsu Tetrahedron Letters, 1988 ,  vol. 29,  # 40  p. 5143 - 5146

Full Text: HTML

Citation Number: 19

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. ... Salinomycin was synthesized from D-glucose, D-mannitol, and ethyl L-lactate via coupling of C1–C9, C10–C17, and C18–C30 segments. Benzyl-type protecting groups as well as regio and stereoselective reactions played a crucial role. ... Salinomycin (1) was synthesized via ...

 Related Synthetic Route
(2R,3R,6S)-6-[(2R,5R,6S)-5-benzyloxy-5-ethyl-6-methyltetrahydropyran-2-yl]-3,6-bis(tert-butyldimethylsilyloxy)-2-(4-methoxybenzyloxy)heptan-1-ol Structure

120269-75-2

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

~%

(2R,3R,6S)-3,6-bis(tert-butyldimethylsilyloxy)-6-[(2R,5R,6S)-5-ethyl-5-(4-methoxybenzyloxy)-6-methyltetrahydropyran-2-yl]-2-(4-methoxybenzyloxy)heptan-1-ol Structure

120269-83-2

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

(2R,3R,6S)-6-[(2R,5R,6S)-5-benzyloxy-5-ethyl-6-methyltetrahydropyran-2-yl]-3,6-bis(tert-butyldimethylsilyloxy)-2-(4-methoxybenzyloxy)heptan-1-ol Structure

120269-75-2

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

~%

(S)-5-((2R,5R,6S)-5-(benzyloxy)-5-ethyl-6-methyltetrahydro-2H-pyran-2-yl)-5-methyldihydrofuran-2(3H)-one Structure

120269-82-1

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

(3R,4R,7S)-7-[(2R,5R,6S)-5-benzyloxy-5-ethyl-6-methyltetrahydropyran-2-yl]-4,7-bis(tert-butyldimethylsilyloxy)-2-(4-methoxybenzyloxy)oct-1-yne Structure

120269-77-4

(3R,4R,7S)-7-[(...

~%

(S)-5-((2R,5R,6S)-5-(benzyloxy)-5-ethyl-6-methyltetrahydro-2H-pyran-2-yl)-5-methyldihydrofuran-2(3H)-one Structure

120269-82-1

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

(2S,3R,6R)-6-[(2R,5R,6S)-5-benzyloxy-5-ethyl-6-methyltetrahydropyran-2-yl]-3,6-bis(tert-butyldimethylsilyloxy)-2-(4-methoxybenzyloxy)heptanal Structure

126365-91-1

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

~%

(S)-5-((2R,5R,6S)-5-(benzyloxy)-5-ethyl-6-methyltetrahydro-2H-pyran-2-yl)-5-methyldihydrofuran-2(3H)-one Structure

120269-82-1

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

(2S,5R,6R)-2-[(2R,5R,6S)-5-benzyloxy-5-ethyl-6-methyltetrahydropyran-2-yl]-8-[(2RS,3R,5S,6S)-6-[(1S,2R)-1-ethyl-2-hydroxybutyl]-2-methoxy-3,5-dimethyltetrahydropyran-2-yl]-6-(4-methoxybenzyloxy)oct-7-yne-2,5-diol Structure

120269-78-5

(2S,5R,6R)-2-[(...

~%

(S)-5-((2R,5R,6S)-5-(benzyloxy)-5-ethyl-6-methyltetrahydro-2H-pyran-2-yl)-5-methyldihydrofuran-2(3H)-one Structure

120269-82-1

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

(2R,3R,6S)-6-((2R,5R,6S)-5-(benzyloxy)-5-ethyl-6-methyltetrahydro-2H-pyran-2-yl)-2-((4-methoxybenzyl)oxy)heptane-1,3,6-triol Structure

120269-74-1

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

~%

(S)-5-((2R,5R,6S)-5-(benzyloxy)-5-ethyl-6-methyltetrahydro-2H-pyran-2-yl)-5-methyldihydrofuran-2(3H)-one Structure

120269-82-1

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

(S)-2-[(2R,3S,6R)-6-[(S)-1-(benzyloxymethyl)propyl]-3-methyltetrahydropyran-2-yl]propan-1-ol Structure

107207-23-8

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

~%

21-epi-20-O-(4-methoxybenzyl)-28-O-benzylsalinomycin Structure

120269-81-0

21-epi-20-O-(4-...

(2R,3R,6S)-6-[(2R,5R,6S)-5-benzyloxy-5-ethyl-6-methyltetrahydropyran-2-yl]-3,6-bis(tert-butyldimethylsilyloxy)-2-(4-methoxybenzyloxy)heptan-1-ol Structure

120269-75-2

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

~%

(2S,5R,6R)-2-[(2R,5R,6S)-5-benzyloxy-5-ethyl-6-methyltetrahydropyran-2-yl]-8-[(2RS,3R,5S,6S)-6-[(1S,2R)-1-ethyl-2-hydroxybutyl]-2-methoxy-3,5-dimethyltetrahydropyran-2-yl]-6-(4-methoxybenzyloxy)oct-7-yne-2,5-diol Structure

120269-78-5

(2S,5R,6R)-2-[(...

(2S,3R,6R)-6-[(2R,5R,6S)-5-benzyloxy-5-ethyl-6-methyltetrahydropyran-2-yl]-3,6-bis(tert-butyldimethylsilyloxy)-2-(4-methoxybenzyloxy)heptanal Structure

126365-91-1

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

~%

(2S,5R,6R)-2-[(2R,5R,6S)-5-benzyloxy-5-ethyl-6-methyltetrahydropyran-2-yl]-8-[(2RS,3R,5S,6S)-6-[(1S,2R)-1-ethyl-2-hydroxybutyl]-2-methoxy-3,5-dimethyltetrahydropyran-2-yl]-6-(4-methoxybenzyloxy)oct-7-yne-2,5-diol Structure

120269-78-5

(2S,5R,6R)-2-[(...

(2R,3R,6S)-6-((2R,5R,6S)-5-(benzyloxy)-5-ethyl-6-methyltetrahydro-2H-pyran-2-yl)-2-((4-methoxybenzyl)oxy)heptane-1,3,6-triol Structure

120269-74-1

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

~%

(2S,5R,6R)-2-[(2R,5R,6S)-5-benzyloxy-5-ethyl-6-methyltetrahydropyran-2-yl]-8-[(2RS,3R,5S,6S)-6-[(1S,2R)-1-ethyl-2-hydroxybutyl]-2-methoxy-3,5-dimethyltetrahydropyran-2-yl]-6-(4-methoxybenzyloxy)oct-7-yne-2,5-diol Structure

120269-78-5

(2S,5R,6R)-2-[(...

(3R,4R,7S)-7-[(2R,5R,6S)-5-benzyloxy-5-ethyl-6-methyltetrahydropyran-2-yl]-4,7-bis(tert-butyldimethylsilyloxy)-2-(4-methoxybenzyloxy)oct-1-yne Structure

120269-77-4

(3R,4R,7S)-7-[(...

~%

(2S,5R,6R)-2-[(2R,5R,6S)-5-benzyloxy-5-ethyl-6-methyltetrahydropyran-2-yl]-8-[(2RS,3R,5S,6S)-6-[(1S,2R)-1-ethyl-2-hydroxybutyl]-2-methoxy-3,5-dimethyltetrahydropyran-2-yl]-6-(4-methoxybenzyloxy)oct-7-yne-2,5-diol Structure

120269-78-5

(2S,5R,6R)-2-[(...

(S)-2-[(2R,3S,6R)-6-[(S)-1-(benzyloxymethyl)propyl]-3-methyltetrahydropyran-2-yl]propan-1-ol Structure

107207-23-8

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

~%

salinomycin acid Structure

120330-27-0

salinomycin acid

(S)-2-[(2R,3S,6R)-6-[(S)-1-(benzyloxymethyl)propyl]-3-methyltetrahydropyran-2-yl]propan-1-ol Structure

107207-23-8

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

~%

21-epi-20,28-bis-O-(4-methoxybenzyl)salinomycin Structure

120269-90-1

21-epi-20,28-bi...

(2R,3R,6S)-6-[(2R,5R,6S)-5-benzyloxy-5-ethyl-6-methyltetrahydropyran-2-yl]-3,6-bis(tert-butyldimethylsilyloxy)-2-(4-methoxybenzyloxy)heptan-1-ol Structure

120269-75-2

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

~98%

(2S,3R,6R)-6-[(2R,5R,6S)-5-benzyloxy-5-ethyl-6-methyltetrahydropyran-2-yl]-3,6-bis(tert-butyldimethylsilyloxy)-2-(4-methoxybenzyloxy)heptanal Structure

126365-91-1

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

(2R,3R,6S)-6-[(2R,5R,6S)-5-benzyloxy-5-ethyl-6-methyltetrahydropyran-2-yl]-3,6-bis(tert-butyldimethylsilyloxy)-2-(4-methoxybenzyloxy)heptan-1-ol Structure

120269-75-2

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

~%

(2S,5R,7R,9S,10S,12R,13Z,15R)-9-[(R)-1-ethyl-2-oxobutyl]-2-[(2R,5R,6S)-5-ethyl-5-(4-methoxybenzyloxy)-6-methyltetrahydropyran-2-yl]-15-(4-methoxybenzyloxy)-2,10,12-trimethyl-1,6,8-trioxadispiro[4.1.5.3]pentadec-13-ene Structure

120269-89-8

(2S,5R,7R,9S,10...

(2R,3R,6S)-3,6-bis(tert-butyldimethylsilyloxy)-6-[(2R,5R,6S)-5-ethyl-5-(4-methoxybenzyloxy)-6-methyltetrahydropyran-2-yl]-2-(4-methoxybenzyloxy)heptan-1-ol Structure

120269-83-2

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

~%

(2S,5R,7R,9S,10S,12R,13Z,15R)-9-[(R)-1-ethyl-2-oxobutyl]-2-[(2R,5R,6S)-5-ethyl-5-(4-methoxybenzyloxy)-6-methyltetrahydropyran-2-yl]-15-(4-methoxybenzyloxy)-2,10,12-trimethyl-1,6,8-trioxadispiro[4.1.5.3]pentadec-13-ene Structure

120269-89-8

(2S,5R,7R,9S,10...

(3R,4R,7S)-4,7-bis(tert-butyldimethylsilyloxy)-7-[(2R,5R,6S)-5-ethyl-5-(4-methoxybenzyloxy)-6-methyltetrahydropyran-2-yl]-3-(4-methoxybenzyloxy)oct-1-yne Structure

120269-85-4

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

~%

(2S,5R,7R,9S,10S,12R,13Z,15R)-9-[(R)-1-ethyl-2-oxobutyl]-2-[(2R,5R,6S)-5-ethyl-5-(4-methoxybenzyloxy)-6-methyltetrahydropyran-2-yl]-15-(4-methoxybenzyloxy)-2,10,12-trimethyl-1,6,8-trioxadispiro[4.1.5.3]pentadec-13-ene Structure

120269-89-8

(2S,5R,7R,9S,10...

(2R,3R,6S)-6-((2R,5R,6S)-5-(benzyloxy)-5-ethyl-6-methyltetrahydro-2H-pyran-2-yl)-2-((4-methoxybenzyl)oxy)heptane-1,3,6-triol Structure

120269-74-1

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

~%

(2S,5R,7R,9S,10S,12R,13Z,15R)-9-[(R)-1-ethyl-2-oxobutyl]-2-[(2R,5R,6S)-5-ethyl-5-(4-methoxybenzyloxy)-6-methyltetrahydropyran-2-yl]-15-(4-methoxybenzyloxy)-2,10,12-trimethyl-1,6,8-trioxadispiro[4.1.5.3]pentadec-13-ene Structure

120269-89-8

(2S,5R,7R,9S,10...


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