e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

Total synthesis of pseudomonic acid C

…, HL Lee, T Mitt, G Pizzolato, EG Baggiolini…

Index: Barrish, Joel C.; Lee, Hsi Lin; Mitt, Toomas; Pizzolato, Giacomo; Baggiolini, Enrico G; Uskokovic, Milan R Journal of Organic Chemistry, 1988 , vol. 53, # 18 p. 4282 - 4295

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Citation Number: 40

Abstract

Two approaches to the synthesis of aldehyde 28, a key intermediate in the total synthesis of pseudomonic acid C, were developed. One asymmetric route from the chiral hydroxy ester 11 proceeded in 13 steps via the hydroxy lactone 17. A shorter approach involved the Lewis acid catalyzed cycloaddition of formaldehyde to the chiral diene 23a to give 22a, which was separated from its diastereomer and then converted into 28 in seven steps. The ...

[2S-[2α(E),3β,4β,5α(2E,4S*,5R*)]]-9-[[3-methyl-1-oxo-4-[tetrahydro-3,4-dihydroxy-5-(5-hydroxy-4-methyl-2-hexenyl)-2H-pyran-2-yl]-2-butenyl]oxy]nonanoic acid methyl ester Structure

[2S-[2α(E),3β,4...

~77%

Pseudomonic Acid C Structure

Pseudomonic Acid C

2-((3S,4R,5R,6S)-6-(2-((tert-butyldiphenylsilyl)oxy)ethyl)-4,5-dihydroxytetrahydro-2H-pyran-3-yl)-N,N-dimethylacetamide Structure

2-((3S,4R,5R,6S...

~%

Pseudomonic Acid C Structure

Pseudomonic Acid C

(3aR-(3aα,4α,7α,7aα))-tetrahydro-N,N,2,2-tetramethyl-4-(2-(((1,1-dimethylethyl)diphenylsilyl)oxy)ethyl)-4H-1,3-dioxolo(4,5-c)pyran-7-acetamide Structure

(3aR-(3aα,4α,7α...

~%

Pseudomonic Acid C Structure

Pseudomonic Acid C

Ethyl (2S,3S)-3-hydroxy-2-methylbutanoate Structure

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

~%

Pseudomonic Acid C Structure

Pseudomonic Acid C

N/A Structure

~%

Pseudomonic Acid C Structure

Pseudomonic Acid C

(S-(R*,S*))-3-(((1,1-dimethylethyl)dimethylsilyl)oxy)-2-methylbutanoic acid ethyl ester Structure

(S-(R*,S*))-3-(...

~%

Pseudomonic Acid C Structure

Pseudomonic Acid C

3,5-hexadienoic acid chloride Structure

3,5-hexadienoic...

~%

Pseudomonic Acid C Structure

Pseudomonic Acid C

2,7-dioxabicyclo[4.3.0]non-4-en-8-one Structure

2,7-dioxabicycl...

~%

Pseudomonic Acid C Structure

Pseudomonic Acid C

(3aS,7R,7aR)-7-iodohexahydro-2H-furo[3,2-b]pyran-2-one Structure

(3aS,7R,7aR)-7-...

~%

Pseudomonic Acid C Structure

Pseudomonic Acid C

(R,E)-N-(1-phenylethyl)hexa-3,5-dienamide Structure

(R,E)-N-(1-phen...

~%

Pseudomonic Acid C Structure

Pseudomonic Acid C

(2S-cis)-5,6-dihydro-N,N-dimethyl-2-[2-[[(1,1-dimethylethyl)diphenylsilyl]oxy]ethyl]-2H-pyran-5-acetamide Structure

(2S-cis)-5,6-di...

~%

Pseudomonic Acid C Structure

Pseudomonic Acid C

[S-(R*,R*)]-5,6-dihydro-N-(1-phenylethyl)-2H-pyran-2-acetamide Structure

[S-(R*,R*)]-5,6...

~%

Pseudomonic Acid C Structure

Pseudomonic Acid C

(5S-cis)-5,6-dihydro-6-[2-[[(1,1-dimethylethyl)diphenylsilyl]oxy]ethyl]-2H-pyran-5-ol Structure

(5S-cis)-5,6-di...

~%

Pseudomonic Acid C Structure

Pseudomonic Acid C

N/A Structure

~%

Pseudomonic Acid C Structure

Pseudomonic Acid C

N/A Structure

~%

Pseudomonic Acid C Structure

Pseudomonic Acid C

N/A Structure

~%

Pseudomonic Acid C Structure

Pseudomonic Acid C

(2S,3S)-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-methyl-1-(phenylsulfonyl)butane Structure

(2S,3S)-3-[[(1,...

~%

Pseudomonic Acid C Structure

Pseudomonic Acid C

tert-butyl(((2S,3S)-4-iodo-3-methylbutan-2-yl)oxy)dimethylsilane Structure

tert-butyl(((2S...

~%

Pseudomonic Acid C Structure

Pseudomonic Acid C

(S)-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-methyl-1-butanol 4-methylbenzenesulfonate Structure

(S)-3-[[(1,1-di...

~%

Pseudomonic Acid C Structure

Pseudomonic Acid C

(2R,3R,E)-2-((tert-butyldimethylsilyl)oxy)-6-((3aS,4S,7S,7aR)-4-(2-((tert-butyldiphenylsilyl)oxy)ethyl)-2,2-dimethyltetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-yl)-3-methylhex-4-en-1-ol Structure

(2R,3R,E)-2-((t...

~%

Pseudomonic Acid C Structure

Pseudomonic Acid C

tert-butyl(2-((3aS,4S,7S,7aR)-7-((4R,5R,E)-5-((tert-butyldimethylsilyl)oxy)-6-iodo-4-methylhex-2-en-1-yl)-2,2-dimethyltetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-4-yl)ethoxy)diphenylsilane Structure

tert-butyl(2-((...

~%

Pseudomonic Acid C Structure

Pseudomonic Acid C

(3aS-(3aα,4α,7aα,7α(3E,2S*)))-tetrahydro-2,2-dimethyl-4-(2-(((1,1-dimethylethyl)diphenylsilyl)oxy)ethyl)-α-(1-propenyl)-4H-1,3-dioxolo(4,5-c)pyran-7-ethanol Structure

(3aS-(3aα,4α,7a...

~%

Pseudomonic Acid C Structure

Pseudomonic Acid C

N/A Structure

~%

Pseudomonic Acid C Structure

Pseudomonic Acid C

(3aS)-(3aα,4α,7aα,7α))-1-(tetrahydro-2,2-dimethyl-4-(2-(((1,1-dimethylethyl)diphenylsilyl)oxy)ethyl)-1,3-dioxolo(4,5-c)pyran-7-yl)-3-pentyn-2-one Structure

(3aS)-(3aα,4α,7...

~%

Pseudomonic Acid C Structure

Pseudomonic Acid C

N/A Structure

~%

Pseudomonic Acid C Structure

Pseudomonic Acid C

benzyl 2-[tert-butyl(dimethyl)silyl]oxyacetate Structure

benzyl 2-[tert-...

~96%

2-(tert-butyldimethylsilyloxy)acetic acid Structure

2-(tert-butyldi...

Benzyl bromide Structure

~%

benzyl 2-[tert-butyl(dimethyl)silyl]oxyacetate Structure

benzyl 2-[tert-...

Enantiospecific total synthesis of pseudomonic acids from ar...

[Fleet, G. W. J.; Gough, M. J.; Shing, T. K. M. Tetrahedron Letters, 1983 , vol. 24, # 34 p. 3661 - 3664]

Enantiospecific total synthesis of pseudomonic acids from ar...

[Fleet, G. W. J.; Gough, M. J.; Shing, T. K. M. Tetrahedron Letters, 1983 , vol. 24, # 34 p. 3661 - 3664]