Direct generation of triketide stereopolyads via merged redox-construction events: total synthesis of (+)-zincophorin methyl ester

…, X Gao, RM Lipinski, MJ Krische

Index: Del Valle, David J.; Krische, Michael J. Journal of the American Chemical Society, 2013 , vol. 135, # 30 p. 10986 - 10989

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Citation Number: 12

Abstract

(+)-Zincophorin methyl ester is prepared in 13 steps (longest linear sequence). A bidirectional redox-triggered double anti-crotylation of 2-methyl-1, 3-propane diol directly assembles the triketide stereopolyad spanning C4–C12, significantly enhancing step

 Related Synthetic Route
Allyl alcohol Structure

107-18-6

Allyl alcohol

Tosyl chloride Structure

98-59-9

Tosyl chloride

~96%

allyl toluene-4-sulfonate Structure

4873-09-0

allyl toluene-4...

1-(methoxymethoxy)-3-nitro-5-vinylbenzene Structure

1447811-32-6

1-(methoxymetho...

~%

[(4E,10Z,12E,14E)-6,22-dihydroxy-16-methoxy-5,7-dimethyl-18-oxo-19-azabicyclo[18.3.1]tetracosa-1(24),4,10,12,14,20,22-heptaen-8-yl] 2-(cyclohexanecarbonylamino)propanoate Structure

98873-83-7

[(4E,10Z,12E,14...

N/A Structure

1447811-40-6

N/A

~%

[(4E,10Z,12E,14E)-6,22-dihydroxy-16-methoxy-5,7-dimethyl-18-oxo-19-azabicyclo[18.3.1]tetracosa-1(24),4,10,12,14,20,22-heptaen-8-yl] 2-(cyclohexanecarbonylamino)propanoate Structure

98873-83-7

[(4E,10Z,12E,14...

(Z)-5-(3-(methoxymethoxy)-5-nitrophenyl)-2-methylpent-2-en-1-ol Structure

1447811-34-8

(Z)-5-(3-(metho...

~%

[(4E,10Z,12E,14E)-6,22-dihydroxy-16-methoxy-5,7-dimethyl-18-oxo-19-azabicyclo[18.3.1]tetracosa-1(24),4,10,12,14,20,22-heptaen-8-yl] 2-(cyclohexanecarbonylamino)propanoate Structure

98873-83-7

[(4E,10Z,12E,14...

N/A Structure

1447811-35-9

N/A

~%

[(4E,10Z,12E,14E)-6,22-dihydroxy-16-methoxy-5,7-dimethyl-18-oxo-19-azabicyclo[18.3.1]tetracosa-1(24),4,10,12,14,20,22-heptaen-8-yl] 2-(cyclohexanecarbonylamino)propanoate Structure

98873-83-7

[(4E,10Z,12E,14...

1-((5R,6S,Z)-5-(4-methoxybenzyloxy)-4,6-dimethylocta-3,7-dienyl)-3-(methoxymethoxy)-5-nitrobenzene Structure

1447811-42-8

1-((5R,6S,Z)-5-...

~%

[(4E,10Z,12E,14E)-6,22-dihydroxy-16-methoxy-5,7-dimethyl-18-oxo-19-azabicyclo[18.3.1]tetracosa-1(24),4,10,12,14,20,22-heptaen-8-yl] 2-(cyclohexanecarbonylamino)propanoate Structure

98873-83-7

[(4E,10Z,12E,14...

(2R,3R,Z)-3-((4-methoxybenzyl)oxy)-7-(3-(methoxymethoxy)-5-nitrophenyl)-2,4-dimethylhept-4-enal Structure

1447811-43-9

(2R,3R,Z)-3-((4...

~%

[(4E,10Z,12E,14E)-6,22-dihydroxy-16-methoxy-5,7-dimethyl-18-oxo-19-azabicyclo[18.3.1]tetracosa-1(24),4,10,12,14,20,22-heptaen-8-yl] 2-(cyclohexanecarbonylamino)propanoate Structure

98873-83-7

[(4E,10Z,12E,14...

N/A Structure

1447811-44-0

N/A

~%

[(4E,10Z,12E,14E)-6,22-dihydroxy-16-methoxy-5,7-dimethyl-18-oxo-19-azabicyclo[18.3.1]tetracosa-1(24),4,10,12,14,20,22-heptaen-8-yl] 2-(cyclohexanecarbonylamino)propanoate Structure

98873-83-7

[(4E,10Z,12E,14...

N/A Structure

1447811-36-0

N/A

~%

[(4E,10Z,12E,14E)-6,22-dihydroxy-16-methoxy-5,7-dimethyl-18-oxo-19-azabicyclo[18.3.1]tetracosa-1(24),4,10,12,14,20,22-heptaen-8-yl] 2-(cyclohexanecarbonylamino)propanoate Structure

98873-83-7

[(4E,10Z,12E,14...

N/A Structure

1447811-37-1

N/A

~%

[(4E,10Z,12E,14E)-6,22-dihydroxy-16-methoxy-5,7-dimethyl-18-oxo-19-azabicyclo[18.3.1]tetracosa-1(24),4,10,12,14,20,22-heptaen-8-yl] 2-(cyclohexanecarbonylamino)propanoate Structure

98873-83-7

[(4E,10Z,12E,14...

N/A Structure

1447811-45-1

N/A

~%

[(4E,10Z,12E,14E)-6,22-dihydroxy-16-methoxy-5,7-dimethyl-18-oxo-19-azabicyclo[18.3.1]tetracosa-1(24),4,10,12,14,20,22-heptaen-8-yl] 2-(cyclohexanecarbonylamino)propanoate Structure

98873-83-7

[(4E,10Z,12E,14...

N/A Structure

1447811-38-2

N/A

~%

[(4E,10Z,12E,14E)-6,22-dihydroxy-16-methoxy-5,7-dimethyl-18-oxo-19-azabicyclo[18.3.1]tetracosa-1(24),4,10,12,14,20,22-heptaen-8-yl] 2-(cyclohexanecarbonylamino)propanoate Structure

98873-83-7

[(4E,10Z,12E,14...

(R,E)-3-methoxy-hepta-4,6-dienoic acid Structure

1071851-04-1

(R,E)-3-methoxy...

~%

[(4E,10Z,12E,14E)-6,22-dihydroxy-16-methoxy-5,7-dimethyl-18-oxo-19-azabicyclo[18.3.1]tetracosa-1(24),4,10,12,14,20,22-heptaen-8-yl] 2-(cyclohexanecarbonylamino)propanoate Structure

98873-83-7

[(4E,10Z,12E,14...

(S,Z)-2-hydroxyhexa-3,5-dienyl 4-methylbenzenesulfonate Structure

1270942-90-9

(S,Z)-2-hydroxy...

~%

[(4E,10Z,12E,14E)-6,22-dihydroxy-16-methoxy-5,7-dimethyl-18-oxo-19-azabicyclo[18.3.1]tetracosa-1(24),4,10,12,14,20,22-heptaen-8-yl] 2-(cyclohexanecarbonylamino)propanoate Structure

98873-83-7

[(4E,10Z,12E,14...

(S,Z)-2-methoxyhexa-3,5-dienyl 4-methylbenzenesulfonate Structure

1270942-91-0

(S,Z)-2-methoxy...

~%

[(4E,10Z,12E,14E)-6,22-dihydroxy-16-methoxy-5,7-dimethyl-18-oxo-19-azabicyclo[18.3.1]tetracosa-1(24),4,10,12,14,20,22-heptaen-8-yl] 2-(cyclohexanecarbonylamino)propanoate Structure

98873-83-7

[(4E,10Z,12E,14...

N/A Structure

1270942-92-1

N/A

~%

[(4E,10Z,12E,14E)-6,22-dihydroxy-16-methoxy-5,7-dimethyl-18-oxo-19-azabicyclo[18.3.1]tetracosa-1(24),4,10,12,14,20,22-heptaen-8-yl] 2-(cyclohexanecarbonylamino)propanoate Structure

98873-83-7

[(4E,10Z,12E,14...

3-nitro-5-vinylphenol Structure

1447811-39-3

3-nitro-5-vinyl...

~%

[(4E,10Z,12E,14E)-6,22-dihydroxy-16-methoxy-5,7-dimethyl-18-oxo-19-azabicyclo[18.3.1]tetracosa-1(24),4,10,12,14,20,22-heptaen-8-yl] 2-(cyclohexanecarbonylamino)propanoate Structure

98873-83-7

[(4E,10Z,12E,14...


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