European Journal of Organic Chemistry

Asymmetric total syntheses of cochliomycin A and zeaenol

N Jana, S Nanda

Index: Jana, Nandan; Nanda, Samik European Journal of Organic Chemistry, 2012 , # 23 p. 4313 - 4320

Full Text: HTML

Citation Number: 11

Abstract

Abstract The first asymmetric total syntheses of two resorcylic acid lactones (RALs)– cochliomycin A and zeaenol–have been achieved in a divergent way. The main highlight of our strategy involves successful application of stereoselecive Keck allylation and Julia– Kocienski olefination to access an advanced intermediate, by starting from L-tartaric acid as a chiral pool compound. This intermediate is coupled with a trisubstituted benzoic acid to ...

 Related Synthetic Route
3,5-Dimethoxybenzaldehyde Structure

7311-34-4

3,5-Dimethoxybe...

Methyltriphenylphosphonium iodide Structure

2065-66-9

Methyltriphenyl...

~95%

1-ethenyl-3,5-dimethoxybenzene Structure

40243-87-6

1-ethenyl-3,5-d...

3,5-Dimethoxybenzylalcohol Structure

705-76-0

3,5-Dimethoxybe...

~%

1-ethenyl-3,5-dimethoxybenzene Structure

40243-87-6

1-ethenyl-3,5-d...

Methyl 3,5-dimethoxybenzoate Structure

2150-37-0

Methyl 3,5-dime...

~%

1-ethenyl-3,5-dimethoxybenzene Structure

40243-87-6

1-ethenyl-3,5-d...

3,5-Dihydroxybenzoic acid Structure

99-10-5

3,5-Dihydroxybe...

~%

1-ethenyl-3,5-dimethoxybenzene Structure

40243-87-6

1-ethenyl-3,5-d...

Methyl 3,5-dimethoxybenzoate Structure

2150-37-0

Methyl 3,5-dime...

~10%

3,5-Dimethoxybenzylalcohol Structure

705-76-0

3,5-Dimethoxybe...

N/A Structure

866022-02-8

N/A

~%

5,6,7,15-tetrahydroxy-17-methoxy-11-methyl-12-oxabicyclo[12.4.0]octadeca-1(14),2,8,15,17-pentaen-13-one Structure

66018-41-5

5,6,7,15-tetrah...

(4S,5S)-4-[(tert-butyldimethylsilyloxy)methyl]-5-[(S)-1-(4-methoxybenzyloxy)but-3-enyl]-2,2-dimethyl-1,3-dioxolane Structure

1403608-16-1

(4S,5S)-4-[(ter...

~%

5,6,7,15-tetrahydroxy-17-methoxy-11-methyl-12-oxabicyclo[12.4.0]octadeca-1(14),2,8,15,17-pentaen-13-one Structure

66018-41-5

5,6,7,15-tetrah...

{(4S,5S)-5-[(S)-1-(4-methoxybenzyloxy)but-3-enyl]-2,2-dimethyl-1,3-dioxolan-4-yl}methanol Structure

1403608-17-2

{(4S,5S)-5-[(S)...

~%

5,6,7,15-tetrahydroxy-17-methoxy-11-methyl-12-oxabicyclo[12.4.0]octadeca-1(14),2,8,15,17-pentaen-13-one Structure

66018-41-5

5,6,7,15-tetrah...

(4R,5S)-5-[(S)-1-(4-methoxybenzyloxy)but-3-enyl]-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde Structure

1403608-11-6

(4R,5S)-5-[(S)-...

~%

5,6,7,15-tetrahydroxy-17-methoxy-11-methyl-12-oxabicyclo[12.4.0]octadeca-1(14),2,8,15,17-pentaen-13-one Structure

66018-41-5

5,6,7,15-tetrah...

2-hydroxy-4-methoxy-6-vinylbenzaldehyde Structure

1403608-13-8

2-hydroxy-4-met...

~%

5,6,7,15-tetrahydroxy-17-methoxy-11-methyl-12-oxabicyclo[12.4.0]octadeca-1(14),2,8,15,17-pentaen-13-one Structure

66018-41-5

5,6,7,15-tetrah...

(4S,5S)-4-[(R,E)-4-tert-butyldiphenylsilyloxypent-1-enyl]-5-[(S)-1-(4-methoxybenzyloxy)but-3-enyl]-2,2-dimethyl-1,3-dioxolane Structure

1403608-18-3

(4S,5S)-4-[(R,E...

~%

5,6,7,15-tetrahydroxy-17-methoxy-11-methyl-12-oxabicyclo[12.4.0]octadeca-1(14),2,8,15,17-pentaen-13-one Structure

66018-41-5

5,6,7,15-tetrah...

(R,E)-5-{(4S,5S)-5-[(S)-1-(4-methoxybenzyloxy)but-3-enyl]-2,2-dimethyl-1,3-dioxolan-4-yl}pent-4-en-2-ol Structure

1403608-10-5

(R,E)-5-{(4S,5S...

~%

5,6,7,15-tetrahydroxy-17-methoxy-11-methyl-12-oxabicyclo[12.4.0]octadeca-1(14),2,8,15,17-pentaen-13-one Structure

66018-41-5

5,6,7,15-tetrah...

N/A Structure

1403608-19-4

N/A

~%

5,6,7,15-tetrahydroxy-17-methoxy-11-methyl-12-oxabicyclo[12.4.0]octadeca-1(14),2,8,15,17-pentaen-13-one Structure

66018-41-5

5,6,7,15-tetrah...

N/A Structure

1403608-20-7

N/A

~%

5,6,7,15-tetrahydroxy-17-methoxy-11-methyl-12-oxabicyclo[12.4.0]octadeca-1(14),2,8,15,17-pentaen-13-one Structure

66018-41-5

5,6,7,15-tetrah...

3,5-Dimethoxybenzylalcohol Structure

705-76-0

3,5-Dimethoxybe...

~%

5,6,7,15-tetrahydroxy-17-methoxy-11-methyl-12-oxabicyclo[12.4.0]octadeca-1(14),2,8,15,17-pentaen-13-one Structure

66018-41-5

5,6,7,15-tetrah...

N/A Structure

91142-86-8

N/A

~%

5,6,7,15-tetrahydroxy-17-methoxy-11-methyl-12-oxabicyclo[12.4.0]octadeca-1(14),2,8,15,17-pentaen-13-one Structure

66018-41-5

5,6,7,15-tetrah...

3,5-Dimethoxybenzaldehyde Structure

7311-34-4

3,5-Dimethoxybe...

~%

5,6,7,15-tetrahydroxy-17-methoxy-11-methyl-12-oxabicyclo[12.4.0]octadeca-1(14),2,8,15,17-pentaen-13-one Structure

66018-41-5

5,6,7,15-tetrah...

3,5-Dihydroxybenzoic acid Structure

99-10-5

3,5-Dihydroxybe...

~%

5,6,7,15-tetrahydroxy-17-methoxy-11-methyl-12-oxabicyclo[12.4.0]octadeca-1(14),2,8,15,17-pentaen-13-one Structure

66018-41-5

5,6,7,15-tetrah...

Methyl 3,5-dimethoxybenzoate Structure

2150-37-0

Methyl 3,5-dime...

~%

5,6,7,15-tetrahydroxy-17-methoxy-11-methyl-12-oxabicyclo[12.4.0]octadeca-1(14),2,8,15,17-pentaen-13-one Structure

66018-41-5

5,6,7,15-tetrah...

1-ethenyl-3,5-dimethoxybenzene Structure

40243-87-6

1-ethenyl-3,5-d...

~%

5,6,7,15-tetrahydroxy-17-methoxy-11-methyl-12-oxabicyclo[12.4.0]octadeca-1(14),2,8,15,17-pentaen-13-one Structure

66018-41-5

5,6,7,15-tetrah...


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