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

The total synthesis of 12-HETE (12-hydroxyeicosatetraenoic acid) and 12, 20-diHETE

Y Leblanc, BJ Fitzsimmons, J Adams…

Index: Leblanc, Yves; Fitzsimmons, Brian J.; Adams, Julian; Perez, Francoise; Rokach, Joshua Journal of Organic Chemistry, 1986 , vol. 51, # 6 p. 789 - 793

Full Text: HTML

Citation Number: 86

Abstract

2: R= CH20H 12, ZO-dlHETE arachidonic acid by a 12-lipoxygenase enzyme, which is found in platelets' and skin, keratinocytes. 2 The 12-HETE is of particular interest since it has been detected in high concentrations in psoriatic lesions3 and has been shown to possess both chemotactic and chemokinetic properties. The 12 (S)-HETE is also the major lipoxygenase-derived arachidonic acid metabolite produced by the platelet and has been ...

(2Z)-6-oxotetradeca-2,4-dien-8-ynal Structure

(2Z)-6-oxotetra...

~%

2,4-tetradecadien-8-yne-1,6-diol Structure

2,4-tetradecadi...

1-diazo-4-decyn-2-one Structure

1-diazo-4-decyn...

~%

2,4-tetradecadien-8-yne-1,6-diol Structure

2,4-tetradecadi...

3-O-(tert-butyldiphenylsilyl)-1,2-bis-O-(1-methylethylidene)-5(Z)-undecene-1,2(R),3(S),11-tetrol Structure

3-O-(tert-butyl...

~%

(S,6Z,10E)-9-((tert-butyldiphenylsilyl)oxy)-12-oxododeca-6,10-dien-1-yl benzoate Structure

(S,6Z,10E)-9-((...

methyl 9-O-(tert-butyldiphenylsilyl)-10,11-bis-O-(1-methylethylidene)-9(S),10(R),11-trihydroxy-6(Z)-undecenoate Structure

methyl 9-O-(ter...

~%

(S,6Z,10E)-9-((tert-butyldiphenylsilyl)oxy)-12-oxododeca-6,10-dien-1-yl benzoate Structure

(S,6Z,10E)-9-((...

11-O-benzoyl-3-O-(tert-butyldiphenylsilyl)-1,2-bis-O-(1-methylethylidene)-5-undecene-1,2(R),3(S),11-tetrol Structure

11-O-benzoyl-3-...

~%

(S,6Z,10E)-9-((tert-butyldiphenylsilyl)oxy)-12-oxododeca-6,10-dien-1-yl benzoate Structure

(S,6Z,10E)-9-((...

3-O-(tert-butyldiphenylsilyl)-1,2-bis-O-(1-methylethylidene)-5(Z)-undecene-1,2(R),3(S),11-tetrol Structure

3-O-(tert-butyl...

~%

(S,Z)-9-((tert-butyldiphenylsilyl)oxy)-10-oxodec-6-en-1-yl benzoate Structure

(S,Z)-9-((tert-...

methyl 9-O-(tert-butyldiphenylsilyl)-10,11-bis-O-(1-methylethylidene)-9(S),10(R),11-trihydroxy-6(Z)-undecenoate Structure

methyl 9-O-(ter...

~%

(S,Z)-9-((tert-butyldiphenylsilyl)oxy)-10-oxodec-6-en-1-yl benzoate Structure

(S,Z)-9-((tert-...

11-O-benzoyl-3-O-(tert-butyldiphenylsilyl)-1,2-bis-O-(1-methylethylidene)-5-undecene-1,2(R),3(S),11-tetrol Structure

11-O-benzoyl-3-...

~%

(S,Z)-9-((tert-butyldiphenylsilyl)oxy)-10-oxodec-6-en-1-yl benzoate Structure

(S,Z)-9-((tert-...

(2R,3S)-(Z)-3-O-(tert-butyldiphenylsilyl)-5-undecene-1,2,3-triol Structure

(2R,3S)-(Z)-3-O...

~%

[(tert-butyldiphenylsilyl)oxy]-2(E),6(Z)-decedienal Structure

[(tert-butyldip...

methyl 9-O-(tert-butyldiphenylsilyl)-10,11-bis-O-(1-methylethylidene)-9(S),10(R),11-trihydroxy-6(Z)-undecenoate Structure

methyl 9-O-(ter...

~%

11-O-benzoyl-3-O-(tert-butyldiphenylsilyl)-1,2-bis-O-(1-methylethylidene)-5-undecene-1,2(R),3(S),11-tetrol Structure

11-O-benzoyl-3-...

1-diazo-4-decyn-2-one Structure

1-diazo-4-decyn...

~%

methyl 12-[(tert-butyldiphenylsilyl)oxy]-8,10,14-eicosatrien-5-ynoate Structure

methyl 12-[(ter...

2,4-tetradecadien-8-yne-1,6-diol Structure

2,4-tetradecadi...

~%

methyl 12-[(tert-butyldiphenylsilyl)oxy]-8,10,14-eicosatrien-5-ynoate Structure

methyl 12-[(ter...

(2Z)-6-oxotetradeca-2,4-dien-8-ynal Structure

(2Z)-6-oxotetra...

~%

methyl 12-[(tert-butyldiphenylsilyl)oxy]-8,10,14-eicosatrien-5-ynoate Structure

methyl 12-[(ter...

(2Z,4E)-1-((4-methoxyphenyl)diphenylmethoxy)tetradeca-2,4-dien-8-yn-6-ol Structure

(2Z,4E)-1-((4-m...

~%

methyl 12-[(tert-butyldiphenylsilyl)oxy]-8,10,14-eicosatrien-5-ynoate Structure

methyl 12-[(ter...

6-[(tert-butyldiphenylsilyl)oxy]-1-[diphenyl(4-methoxyphenyl)methoxy]-2,4-tetradecadien-8-yne Structure

6-[(tert-butyld...

~%

methyl 12-[(tert-butyldiphenylsilyl)oxy]-8,10,14-eicosatrien-5-ynoate Structure

methyl 12-[(ter...

6-[(tert-butyldiphenylsilyl)oxy]-1-[diphenyl(4-methoxyphenyl)methoxy]-2,4,8-tetradecatriene Structure

6-[(tert-butyld...

~%

methyl 12-[(tert-butyldiphenylsilyl)oxy]-8,10,14-eicosatrien-5-ynoate Structure

methyl 12-[(ter...

6-[(tert-butyldiphenylsilyl)oxy]-2,4,8-tetradecatrien-1-ol Structure

6-[(tert-butyld...

~%

methyl 12-[(tert-butyldiphenylsilyl)oxy]-8,10,14-eicosatrien-5-ynoate Structure

methyl 12-[(ter...

methyl 9-O-(tert-butyldiphenylsilyl)-10,11-bis-O-(1-methylethylidene)-9(S),10(R),11-trihydroxy-6(Z)-undecenoate Structure

methyl 9-O-(ter...

~71%

3-O-(tert-butyldiphenylsilyl)-1,2-bis-O-(1-methylethylidene)-5(Z)-undecene-1,2(R),3(S),11-tetrol Structure

3-O-(tert-butyl...

6-[(tert-butyldiphenylsilyl)oxy]-2,4,8-tetradecatrien-1-ol Structure

6-[(tert-butyld...

~97%

1-bromo-6-[(tert-butyldiphenylsilyl)oxy]-2,4,8-tetradecatriene Structure

1-bromo-6-[(ter...

2,4-tetradecadien-8-yne-1,6-diol Structure

2,4-tetradecadi...

~%

1-bromo-6-[(tert-butyldiphenylsilyl)oxy]-2,4,8-tetradecatriene Structure

1-bromo-6-[(ter...

(2Z)-6-oxotetradeca-2,4-dien-8-ynal Structure

(2Z)-6-oxotetra...

~%

1-bromo-6-[(tert-butyldiphenylsilyl)oxy]-2,4,8-tetradecatriene Structure

1-bromo-6-[(ter...

(2Z,4E)-1-((4-methoxyphenyl)diphenylmethoxy)tetradeca-2,4-dien-8-yn-6-ol Structure

(2Z,4E)-1-((4-m...

~%

1-bromo-6-[(tert-butyldiphenylsilyl)oxy]-2,4,8-tetradecatriene Structure

1-bromo-6-[(ter...

6-[(tert-butyldiphenylsilyl)oxy]-1-[diphenyl(4-methoxyphenyl)methoxy]-2,4-tetradecadien-8-yne Structure

6-[(tert-butyld...

~%

1-bromo-6-[(tert-butyldiphenylsilyl)oxy]-2,4,8-tetradecatriene Structure

1-bromo-6-[(ter...

6-[(tert-butyldiphenylsilyl)oxy]-1-[diphenyl(4-methoxyphenyl)methoxy]-2,4,8-tetradecatriene Structure

6-[(tert-butyld...

~%

1-bromo-6-[(tert-butyldiphenylsilyl)oxy]-2,4,8-tetradecatriene Structure

1-bromo-6-[(ter...

(2R,3S)-(Z)-3-O-(tert-butyldiphenylsilyl)-5-undecene-1,2,3-triol Structure

(2R,3S)-(Z)-3-O...

~93%

2(S)-[(tert-butyldiphenylsilyl)oxy]-4(Z)-decenal Structure

2(S)-[(tert-but...

1-diazo-4-decyn-2-one Structure

1-diazo-4-decyn...

~%

6-[(tert-butyldiphenylsilyl)oxy]-2,4,8-tetradecatrien-1-ol Structure

6-[(tert-butyld...

2,4-tetradecadien-8-yne-1,6-diol Structure

2,4-tetradecadi...

~%

6-[(tert-butyldiphenylsilyl)oxy]-2,4,8-tetradecatrien-1-ol Structure

6-[(tert-butyld...

(2Z)-6-oxotetradeca-2,4-dien-8-ynal Structure

(2Z)-6-oxotetra...

~%

6-[(tert-butyldiphenylsilyl)oxy]-2,4,8-tetradecatrien-1-ol Structure

6-[(tert-butyld...

(2Z,4E)-1-((4-methoxyphenyl)diphenylmethoxy)tetradeca-2,4-dien-8-yn-6-ol Structure

(2Z,4E)-1-((4-m...

~%

6-[(tert-butyldiphenylsilyl)oxy]-2,4,8-tetradecatrien-1-ol Structure

6-[(tert-butyld...

6-[(tert-butyldiphenylsilyl)oxy]-1-[diphenyl(4-methoxyphenyl)methoxy]-2,4-tetradecadien-8-yne Structure

6-[(tert-butyld...

~%

6-[(tert-butyldiphenylsilyl)oxy]-2,4,8-tetradecatrien-1-ol Structure

6-[(tert-butyld...

6-[(tert-butyldiphenylsilyl)oxy]-1-[diphenyl(4-methoxyphenyl)methoxy]-2,4,8-tetradecatriene Structure

6-[(tert-butyld...

~49%

6-[(tert-butyldiphenylsilyl)oxy]-2,4,8-tetradecatrien-1-ol Structure

6-[(tert-butyld...

1-diazo-4-decyn-2-one Structure

1-diazo-4-decyn...

~%

1-bromo-6-[(tert-butyldiphenylsilyl)oxy]-2,4,8-tetradecatriene Structure

1-bromo-6-[(ter...

6-[(tert-butyldiphenylsilyl)oxy]-1-[diphenyl(4-methoxyphenyl)methoxy]-2,4-tetradecadien-8-yne Structure

6-[(tert-butyld...

~95%

6-[(tert-butyldiphenylsilyl)oxy]-1-[diphenyl(4-methoxyphenyl)methoxy]-2,4,8-tetradecatriene Structure

6-[(tert-butyld...

1-diazo-4-decyn-2-one Structure

1-diazo-4-decyn...

~%

6-[(tert-butyldiphenylsilyl)oxy]-1-[diphenyl(4-methoxyphenyl)methoxy]-2,4,8-tetradecatriene Structure

6-[(tert-butyld...

2,4-tetradecadien-8-yne-1,6-diol Structure

2,4-tetradecadi...

~%

6-[(tert-butyldiphenylsilyl)oxy]-1-[diphenyl(4-methoxyphenyl)methoxy]-2,4,8-tetradecatriene Structure

6-[(tert-butyld...

(2Z)-6-oxotetradeca-2,4-dien-8-ynal Structure

(2Z)-6-oxotetra...

~%

6-[(tert-butyldiphenylsilyl)oxy]-1-[diphenyl(4-methoxyphenyl)methoxy]-2,4,8-tetradecatriene Structure

6-[(tert-butyld...

(2Z,4E)-1-((4-methoxyphenyl)diphenylmethoxy)tetradeca-2,4-dien-8-yn-6-ol Structure

(2Z,4E)-1-((4-m...

~%

6-[(tert-butyldiphenylsilyl)oxy]-1-[diphenyl(4-methoxyphenyl)methoxy]-2,4,8-tetradecatriene Structure

6-[(tert-butyld...

1-diazo-4-decyn-2-one Structure

1-diazo-4-decyn...

~%

6-[(tert-butyldiphenylsilyl)oxy]-1-[diphenyl(4-methoxyphenyl)methoxy]-2,4-tetradecadien-8-yne Structure

6-[(tert-butyld...

2,4-tetradecadien-8-yne-1,6-diol Structure

2,4-tetradecadi...

~%

6-[(tert-butyldiphenylsilyl)oxy]-1-[diphenyl(4-methoxyphenyl)methoxy]-2,4-tetradecadien-8-yne Structure

6-[(tert-butyld...

(2Z)-6-oxotetradeca-2,4-dien-8-ynal Structure

(2Z)-6-oxotetra...

~%

6-[(tert-butyldiphenylsilyl)oxy]-1-[diphenyl(4-methoxyphenyl)methoxy]-2,4-tetradecadien-8-yne Structure

6-[(tert-butyld...

1-diazo-4-decyn-2-one Structure

1-diazo-4-decyn...

~%

(2Z,4E)-1-((4-methoxyphenyl)diphenylmethoxy)tetradeca-2,4-dien-8-yn-6-ol Structure

(2Z,4E)-1-((4-m...

(2Z)-6-oxotetradeca-2,4-dien-8-ynal Structure

(2Z)-6-oxotetra...

~%

(2Z,4E)-1-((4-methoxyphenyl)diphenylmethoxy)tetradeca-2,4-dien-8-yn-6-ol Structure

(2Z,4E)-1-((4-m...