Highly stereocontrolled total synthesis of leukotriene B4, 20-hydroxyleukotriene B4, leukotriene B3, and their analogs

Y Kobayashi, T Shimazaki, H Taguchi…

Index: Kobayashi, Yuichi; Shimazaki, Toshiyuki; Taguchi, Hideki; Sato, Fumie Journal of Organic Chemistry, 1990 , vol. 55, # 19 p. 5324 - 5335

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Citation Number: 74

Abstract

A highly stereocontrolled and practical new method for synthesis of LTB,(l), 20-OH-LTB4 (2), and LTBB (3) has been developed, which uses the palladium-catalyzed coupling reaction of the vinylborane 5, derived from the C (l)-C (9) fragment 4, with the corresponding C (lO)-C (20) fragments 6a-c. The acetylene 4 was synthesized by palladium-copper-catalyzed coupling reaction of (trimethylsily1) acetylene with the bromide 12, which was prepared ...

 Related Synthetic Route
(5S,6Z,8E,10E,12R)-5,12-bis((tert-butyldimethylsilyl)oxy)icosa-6,8,10-trien-14-ynoic acid Structure

129594-44-1

(5S,6Z,8E,10E,1...

~54%

14,15-dehydro leukotriene b4 Structure

114616-11-4

14,15-dehydro l...

1-Bromopentane Structure

110-53-2

1-Bromopentane

~%

14,15-dehydro leukotriene b4 Structure

114616-11-4

14,15-dehydro l...

1-trimethylsilylhex-1-en-5-yn-3-ol Structure

119119-60-7

1-trimethylsily...

~%

14,15-dehydro leukotriene b4 Structure

114616-11-4

14,15-dehydro l...

4-(1'-ethoxyethoxy)-6-(trimethylsilyl)-5(E)-hexen-1-yne Structure

120891-49-8

4-(1'-ethoxyeth...

~%

14,15-dehydro leukotriene b4 Structure

114616-11-4

14,15-dehydro l...

N/A Structure

129594-40-7

N/A

~%

14,15-dehydro leukotriene b4 Structure

114616-11-4

14,15-dehydro l...

1-(trimethylsilyl)-1(E)-undecen-5-yn-3-ol Structure

119238-88-9

1-(trimethylsil...

~%

14,15-dehydro leukotriene b4 Structure

114616-11-4

14,15-dehydro l...

5-Oxo-pentanoic acid methyl ester Structure

6026-86-4

5-Oxo-pentanoic...

~%

14,15-dehydro leukotriene b4 Structure

114616-11-4

14,15-dehydro l...

Methyl (5S)-7-Bromo-5-hydroxyhept-6-enoate Structure

111037-32-2

Methyl (5S)-7-B...

~%

14,15-dehydro leukotriene b4 Structure

114616-11-4

14,15-dehydro l...

N/A Structure

129594-43-0

N/A

~%

14,15-dehydro leukotriene b4 Structure

114616-11-4

14,15-dehydro l...

methyl 7-bromo-5(S)-[(tert-butyldimethylsilyl)oxy]-6(Z)-heptenoate Structure

115418-83-2

methyl 7-bromo-...

~%

14,15-dehydro leukotriene b4 Structure

114616-11-4

14,15-dehydro l...

methyl 5(S)-[(tert-butyldimethylsilyl)oxy]-6(Z)-nonen-8-ynoate Structure

115418-85-4

methyl 5(S)-[(t...

~%

14,15-dehydro leukotriene b4 Structure

114616-11-4

14,15-dehydro l...

(S,Z)-methyl 5-((tert-butyldimethylsilyl)oxy)-9-(trimethylsilyl)non-6-en-8-ynoate Structure

115418-84-3

(S,Z)-methyl 5-...

~%

14,15-dehydro leukotriene b4 Structure

114616-11-4

14,15-dehydro l...

N/A Structure

129594-41-8

N/A

~%

14,15-dehydro leukotriene b4 Structure

114616-11-4

14,15-dehydro l...

N/A Structure

119119-05-0

N/A

~%

14,15-dehydro leukotriene b4 Structure

114616-11-4

14,15-dehydro l...

methyl 5-hydroxy-7-(trimethylsilyl)-6(E)-heptenoate Structure

115418-81-0

methyl 5-hydrox...

~%

14,15-dehydro leukotriene b4 Structure

114616-11-4

14,15-dehydro l...

methyl 5(S)-hydroxy-7-(trimethylsilyl)-6(E)-heptenoate Structure

115461-52-4

methyl 5(S)-hyd...

~%

14,15-dehydro leukotriene b4 Structure

114616-11-4

14,15-dehydro l...

N/A Structure

129704-38-7

N/A

~%

14,15-dehydro leukotriene b4 Structure

114616-11-4

14,15-dehydro l...

N/A Structure

119119-61-8

N/A

~%

14,15-dehydro leukotriene b4 Structure

114616-11-4

14,15-dehydro l...

5-iodo-1-pentanol Structure

67133-88-4

5-iodo-1-pentanol

~%

LTB4_20-hydroxy Structure

79516-82-8

LTB4_20-hydroxy

5-hydroxypentyl 4-methylbenzenesulfonate Structure

95769-37-2

5-hydroxypentyl...

~%

LTB4_20-hydroxy Structure

79516-82-8

LTB4_20-hydroxy

1-(1'-ethoxyethoxy)-5-iodopentane Structure

129594-25-8

1-(1'-ethoxyeth...

~%

LTB4_20-hydroxy Structure

79516-82-8

LTB4_20-hydroxy

1-trimethylsilylhex-1-en-5-yn-3-ol Structure

119119-60-7

1-trimethylsily...

~%

LTB4_20-hydroxy Structure

79516-82-8

LTB4_20-hydroxy

11-(trimethylsilyl)-6(Z),10(E)-undecadiene-1,9-diol Structure

129594-28-1

11-(trimethylsi...

~%

LTB4_20-hydroxy Structure

79516-82-8

LTB4_20-hydroxy

4-(1'-ethoxyethoxy)-6-(trimethylsilyl)-5(E)-hexen-1-yne Structure

120891-49-8

4-(1'-ethoxyeth...

~%

LTB4_20-hydroxy Structure

79516-82-8

LTB4_20-hydroxy

3,11-bis(1'-ethoxyethoxy)-1-(trimethylsilyl)-1(E)-undecen-5-yne Structure

129594-26-9

3,11-bis(1'-eth...

~%

LTB4_20-hydroxy Structure

79516-82-8

LTB4_20-hydroxy

N/A Structure

129594-27-0

N/A

~%

LTB4_20-hydroxy Structure

79516-82-8

LTB4_20-hydroxy

11-[(tert-butyldimethylsilyl)oxy]-1-(trimethylsilyl)-1(E),5(Z)-undecadien-3-ol Structure

129594-29-2

11-[(tert-butyl...

~%

LTB4_20-hydroxy Structure

79516-82-8

LTB4_20-hydroxy

5-Oxo-pentanoic acid methyl ester Structure

6026-86-4

5-Oxo-pentanoic...

~%

LTB4_20-hydroxy Structure

79516-82-8

LTB4_20-hydroxy

Methyl (5S)-7-Bromo-5-hydroxyhept-6-enoate Structure

111037-32-2

Methyl (5S)-7-B...

~%

LTB4_20-hydroxy Structure

79516-82-8

LTB4_20-hydroxy

N/A Structure

129594-32-7

N/A

~%

LTB4_20-hydroxy Structure

79516-82-8

LTB4_20-hydroxy

methyl 7-bromo-5(S)-[(tert-butyldimethylsilyl)oxy]-6(Z)-heptenoate Structure

115418-83-2

methyl 7-bromo-...

~%

LTB4_20-hydroxy Structure

79516-82-8

LTB4_20-hydroxy

methyl 5(S)-[(tert-butyldimethylsilyl)oxy]-6(Z)-nonen-8-ynoate Structure

115418-85-4

methyl 5(S)-[(t...

~%

LTB4_20-hydroxy Structure

79516-82-8

LTB4_20-hydroxy

3(R),11-bis[(tert-butyldimethylsilyl)oxy]-1-iodo-1(E),5(Z)-undecadiene Structure

129594-33-8

3(R),11-bis[(te...

~%

LTB4_20-hydroxy Structure

79516-82-8

LTB4_20-hydroxy

(S,Z)-methyl 5-((tert-butyldimethylsilyl)oxy)-9-(trimethylsilyl)non-6-en-8-ynoate Structure

115418-84-3

(S,Z)-methyl 5-...

~%

LTB4_20-hydroxy Structure

79516-82-8

LTB4_20-hydroxy

(R,Z)-9-((tert-butyldimethylsilyl)oxy)-1-((2S,3S)-3-(trimethylsilyl)oxiran-2-yl)non-3-en-1-yl 4-nitrobenzoate Structure

129594-31-6

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

~%

LTB4_20-hydroxy Structure

79516-82-8

LTB4_20-hydroxy

methyl 5-hydroxy-7-(trimethylsilyl)-6(E)-heptenoate Structure

115418-81-0

methyl 5-hydrox...

~%

LTB4_20-hydroxy Structure

79516-82-8

LTB4_20-hydroxy

methyl 5(S)-hydroxy-7-(trimethylsilyl)-6(E)-heptenoate Structure

115461-52-4

methyl 5(S)-hyd...

~%

LTB4_20-hydroxy Structure

79516-82-8

LTB4_20-hydroxy

11-[(tert-butyldimethylsilyl)oxy]-1-(trimethylsilyl)-1(E),5(Z)-undecadien-3(S)-ol Structure

129704-33-2

11-[(tert-butyl...

~%

LTB4_20-hydroxy Structure

79516-82-8

LTB4_20-hydroxy

(S,Z)-9-((tert-butyldimethylsilyl)oxy)-1-((2S,3S)-3-(trimethylsilyl)oxiran-2-yl)non-3-en-1-ol Structure

129704-34-3

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

~%

LTB4_20-hydroxy Structure

79516-82-8

LTB4_20-hydroxy

2(S)-[9'-(tert-butyldimethylsilyl)oxy]-1'(R)-hydroxy-3'(Z)-nonenyl-3(S)-(trimethylsilyl)oxirane Structure

129704-35-4

2(S)-[9'-(tert-...

~%

LTB4_20-hydroxy Structure

79516-82-8

LTB4_20-hydroxy

N/A Structure

129594-30-5

N/A

~%

LTB4_20-hydroxy Structure

79516-82-8

LTB4_20-hydroxy

5(S),12(R),20-tris[(tert-butyldimethylislyl)oxy]-6(Z),8(E),10(E),14(Z)-eicosatetraenoic acid Structure

129594-38-3

5(S),12(R),20-t...

~78%

LTB4_20-hydroxy Structure

79516-82-8

LTB4_20-hydroxy

1,5-Pentanediol Structure

111-29-5

1,5-Pentanediol

~%

LTB4_20-hydroxy Structure

79516-82-8

LTB4_20-hydroxy

1,1-diethoxynon-3-yne Structure

90290-02-1

1,1-diethoxynon...

~%

(Z)-3-nonen-1-al Structure

31823-43-5

(Z)-3-nonen-1-al

Hept-1-yne Structure

628-71-7

Hept-1-yne

~%

1-trimethylsilylundeca-1,5-dien-3-ol Structure

115418-86-5

1-trimethylsily...

1,1-diethoxynon-3-yne Structure

90290-02-1

1,1-diethoxynon...

~%

1-trimethylsilylundeca-1,5-dien-3-ol Structure

115418-86-5

1-trimethylsily...

1,1-diethoxynon-3-ene Structure

89682-47-3

1,1-diethoxynon...

~%

1-trimethylsilylundeca-1,5-dien-3-ol Structure

115418-86-5

1-trimethylsily...

5(S),12(R)-bis[(tert-butyldimethylsilyl)oxy]-6(7),8(E),10(E),14(Z)-eicosatetraenoic acid Structure

115418-91-2

5(S),12(R)-bis[...

~87%

Leukotriene B4 Structure

71160-24-2

Leukotriene B4

trans-3-(trimethylsilyl)acryl-aldehyde Structure

58107-34-9

trans-3-(trimet...

3-Bromopropyne Structure

106-96-7

3-Bromopropyne

~99%

1-trimethylsilylhex-1-en-5-yn-3-ol Structure

119119-60-7

1-trimethylsily...


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