Multi??Step Application of Immobilized Reagents and Scavengers: A Total Synthesis of Epothilone C

…, PS Jackson, DS Brown, IR Baxendale…

Index: Storer, R. Ian; Takemoto, Toshiyasu; Jackson, Philip S.; Brown, Dearg S.; Baxendale, Ian R.; Ley, Steven V. Chemistry - A European Journal, 2004 , vol. 10, # 10 p. 2529 - 2547

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Citation Number: 92

Abstract

Abstract The total synthesis of the cytotoxic antitumour natural product epothilone C has provided a stage for the exploitation and further development of immobilized reagent methods. A stereoselective convergent synthetic strategy was applied, incorporating polymer-supported reagents, catalysts, scavengers and catch-and-release techniques to avoid frequent aqueous work-up and chromatographic purification.

 Related Synthetic Route
(3S,6R,7S,8S,12Z,15S,16E)-3,7-bis(tert-butyldimethylsilyloxy)-15-hydroxy-4,4,6,8,16-pentamethyl-17-(2-methyl-1,3-thiazol-4-yl)-5-oxo-heptadeca-12,16-dienoic acid Structure

188730-19-0

(3S,6R,7S,8S,12...

~%

EPOTHILONE C Structure

186692-73-9

EPOTHILONE C

2-methyl-4-([E]-2'-methylprop-1'-en-3'-ol)thiazole Structure

245040-50-0

2-methyl-4-([E]...

~%

(3S)-2-methyl-1-(2-methyl-1,3-thiazol-4-yl)hexa-1,5-dien-3-ol Structure

187283-46-1

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

BUT-3-ENYLOXY-TERT-BUTYL-DIMETHYL-SILANE Structure

108794-10-1

BUT-3-ENYLOXY-T...

~91%

3-(tert-butyldimethylsilyloxy)propanal Structure

89922-82-7

3-(tert-butyldi...

N/A Structure

188730-18-9

N/A

~%

EPOTHILONE C Structure

186692-73-9

EPOTHILONE C

(3S,6R,7S,8S,12Z,15S,16E)-3,7,15-tris(tert-butyldimethylsilyloxy)-1-hydroxy-4,4,6,8,16-pentamethyl-17-(2-methyl-1,3-thiazol-4-yl)heptadeca-12,16-dien-5-one Structure

583829-95-2

(3S,6R,7S,8S,12...

~%

EPOTHILONE C Structure

186692-73-9

EPOTHILONE C

(3S,6R,7S,8S,12Z,15S,16E)-3,7,15-tris(tert-butyldimethylsilyloxy)-4,4,6,8,16-pentamethyl-17-(2-methyl-1,3-thiazol-4-yl)-5-oxo-heptadeca-12,16-dienal Structure

583829-97-4

(3S,6R,7S,8S,12...

~%

EPOTHILONE C Structure

186692-73-9

EPOTHILONE C

D-phenylalanine Structure

673-06-3

D-phenylalanine

Tosyl chloride Structure

98-59-9

Tosyl chloride

~79%

(R)-2-(4-Methylphenylsulfonamido)-3-phenylpropanoicacid Structure

86117-53-5

(R)-2-(4-Methyl...

2-methyl-4-([E]-2'-methylprop-1'-en-3'-ol)thiazole Structure

245040-50-0

2-methyl-4-([E]...

~60%

(2E)-2-Methyl-3-(2-methyl-1,3-thiazol-4-yl)acrylaldehyde Structure

184246-38-6

(2E)-2-Methyl-3...

(6R)-6-methyl-7-tetrahydropyranyloxyhept-1-ene Structure

583829-93-0

(6R)-6-methyl-7...

~97%

(2S)-2-methylhept-6-en-1-ol Structure

193071-52-2

(2S)-2-methylhe...

(4S)-4,6-bis[[tert-butyl(dimethyl)silyl]oxy]-3,3-dimethylhexan-2-one Structure

218614-14-3

(4S)-4,6-bis[[t...

methyl iodide Structure

74-88-4

methyl iodide

~96%

(5S)-5,7-Bis-{[tert-butyldimethylsilyl)oxy]}-4,4-dimethylheptan-3-one Structure

187527-25-9

(5S)-5,7-Bis-{[...

(-)-METHYL (3S)-3,5-BIS-[(TERT-BUTYLDIMETHYLSILYL)OXY]-2,2-DIMETHYLPENTANOATE Structure

218614-13-2

(-)-METHYL (3S)...

~%

(5S)-5,7-Bis-{[tert-butyldimethylsilyl)oxy]}-4,4-dimethylheptan-3-one Structure

187527-25-9

(5S)-5,7-Bis-{[...

BUT-3-ENYLOXY-TERT-BUTYL-DIMETHYL-SILANE Structure

108794-10-1

BUT-3-ENYLOXY-T...

~%

(5S)-5,7-Bis-{[tert-butyldimethylsilyl)oxy]}-4,4-dimethylheptan-3-one Structure

187527-25-9

(5S)-5,7-Bis-{[...

tert-Butyldimethylsilyl Trifluoromethanesulfonate Structure

69739-34-0

tert-Butyldimet...

~%

(5S)-5,7-Bis-{[tert-butyldimethylsilyl)oxy]}-4,4-dimethylheptan-3-one Structure

187527-25-9

(5S)-5,7-Bis-{[...

N/A Structure

187527-30-6

N/A

~%

(5S)-5,7-Bis-{[tert-butyldimethylsilyl)oxy]}-4,4-dimethylheptan-3-one Structure

187527-25-9

(5S)-5,7-Bis-{[...

(3S)-3,5-bis-(tert-butyldimethylsilyloxy)-2,2-dimethylpentanal Structure

152426-82-9

(3S)-3,5-bis-(t...

~%

(5S)-5,7-Bis-{[tert-butyldimethylsilyl)oxy]}-4,4-dimethylheptan-3-one Structure

187527-25-9

(5S)-5,7-Bis-{[...

3-{[tert-Butyl(dimethyl)silyl]oxy}propan-1-ol Structure

73842-99-6

3-{[tert-Butyl(...

~%

(5S)-5,7-Bis-{[tert-butyldimethylsilyl)oxy]}-4,4-dimethylheptan-3-one Structure

187527-25-9

(5S)-5,7-Bis-{[...

(3S)-2,2-dimethylpent-4-ene-1,3-diol Structure

725738-50-1

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

~%

(5S)-5,7-Bis-{[tert-butyldimethylsilyl)oxy]}-4,4-dimethylheptan-3-one Structure

187527-25-9

(5S)-5,7-Bis-{[...

(3S)-3-hydroxy-2,2-dimethylpent-4-enyl benzoate Structure

725738-51-2

(3S)-3-hydroxy-...

~%

(5S)-5,7-Bis-{[tert-butyldimethylsilyl)oxy]}-4,4-dimethylheptan-3-one Structure

187527-25-9

(5S)-5,7-Bis-{[...

(+/-)-methyl-5-(tert-butyldimethylsilyloxy)-3-hydroxy-2,2-dimethylpentanoate Structure

725738-70-5

(+/-)-methyl-5-...

~%

(5S)-5,7-Bis-{[tert-butyldimethylsilyl)oxy]}-4,4-dimethylheptan-3-one Structure

187527-25-9

(5S)-5,7-Bis-{[...

(3S)-3,5-dihydroxy-2,2-dimethylpentyl benzoate Structure

725738-52-3

(3S)-3,5-dihydr...

~%

(5S)-5,7-Bis-{[tert-butyldimethylsilyl)oxy]}-4,4-dimethylheptan-3-one Structure

187527-25-9

(5S)-5,7-Bis-{[...

(3S)-3,5-bis-(tert-butyldimethylsilyloxy)-2,2-dimethylpentyl benzoate Structure

725738-53-4

(3S)-3,5-bis-(t...

~%

(5S)-5,7-Bis-{[tert-butyldimethylsilyl)oxy]}-4,4-dimethylheptan-3-one Structure

187527-25-9

(5S)-5,7-Bis-{[...

(S)-N-[5-tert-butyldimethylsilyloxy-(3S)-hydroxy-2,2-dimethylpentanoyl]bornane-10,2-sultam Structure

725738-55-6

(S)-N-[5-tert-b...

~%

(5S)-5,7-Bis-{[tert-butyldimethylsilyl)oxy]}-4,4-dimethylheptan-3-one Structure

187527-25-9

(5S)-5,7-Bis-{[...

(S)-N-[(3S),5-bis-tert-butyldimethylsilyloxy-2,2-dimethylpentanoyl]bornane-10,2-sultam Structure

725738-56-7

(S)-N-[(3S),5-b...

~%

(5S)-5,7-Bis-{[tert-butyldimethylsilyl)oxy]}-4,4-dimethylheptan-3-one Structure

187527-25-9

(5S)-5,7-Bis-{[...


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