The Journal of Organic Chemistry

Silicon-mediated skipped diene synthesis. Application to the melon fly pheromone

SR Wilson, PA Zucker

Index: Wilson, Stephen R.; Zucker, Paul A. Journal of Organic Chemistry, 1988 , vol. 53, # 20 p. 4682 - 4693

Full Text: HTML

Citation Number: 42

Abstract

The 1, l-diene unit is a key structural feature of many fatty acid derived natural products including arachidonic acid, several of the leukotrienes, and a variety of insect pheromones. In this paper substituted [2-[(tri-methylsilyl) methyl] cyclopropyl] carbinols are demonstrated to cleave readily, upon treatment with acid or upon conversion to the corresponding mesylates, to give mono-and disubstituted 1, l-pentadienes. Stereoselective formation of ...

 Related Synthetic Route
N/A Structure

943-92-0

N/A

~%

octa-4,7-dienal Structure

56053-82-8

octa-4,7-dienal

(2-((trimethylsilyl)methyl)cyclopropyl)methanol Structure

116264-56-3

(2-((trimethyls...

~%

octa-4,7-dienal Structure

56053-82-8

octa-4,7-dienal

2-((trimethylsilyl)methyl)cyclopropanecarbaldehyde Structure

116264-58-5

2-((trimethylsi...

~%

octa-4,7-dienal Structure

56053-82-8

octa-4,7-dienal

3-(1,3-dioxolan-2-yl)-1-(2-((trimethylsilyl)methyl)cyclopropyl)propan-1-ol Structure

116264-84-7

3-(1,3-dioxolan...

~%

octa-4,7-dienal Structure

56053-82-8

octa-4,7-dienal

N/A Structure

116264-85-8

N/A

3-(1,3-dioxolan-2-yl)-1-(2-((trimethylsilyl)methyl)cyclopropyl)propan-1-ol Structure

116264-84-7

3-(1,3-dioxolan...

~%

octa-4,7-dienal Structure

56053-82-8

octa-4,7-dienal

3-(Trimethylsilyl)-2-propyn-1-ol Structure

5272-36-6

3-(Trimethylsil...

~98%

trans-3-(trimethylsilyl)allyl alcohol Structure

59376-64-6

trans-3-(trimet...

1-(2-((trimethylsilyl)methyl)cyclopropyl)heptan-1-ol Structure

116264-63-2

1-(2-((trimethy...

~59%

1,4-Undecadiene (E) Structure

55976-13-1

1,4-Undecadiene (E)

1-Bromohexane Structure

111-25-1

1-Bromohexane

~%

1,4-Undecadiene (E) Structure

55976-13-1

1,4-Undecadiene (E)

N/A Structure

943-92-0

N/A

~%

1,4-Undecadiene (E) Structure

55976-13-1

1,4-Undecadiene (E)

(2-((trimethylsilyl)methyl)cyclopropyl)methanol Structure

116264-56-3

(2-((trimethyls...

~%

1,4-Undecadiene (E) Structure

55976-13-1

1,4-Undecadiene (E)

2-((trimethylsilyl)methyl)cyclopropanecarbaldehyde Structure

116264-58-5

2-((trimethylsi...

~%

1,4-Undecadiene (E) Structure

55976-13-1

1,4-Undecadiene (E)

((1S,2R)-2-((R)-1-(trimethylsilyl)heptyl)cyclopropyl)methanol Structure

116264-77-8

((1S,2R)-2-((R)...

~%

1,4-Undecadiene (E) Structure

55976-13-1

1,4-Undecadiene (E)

(Z)-1,4-Undecadiene Structure

55976-14-2

(Z)-1,4-Undecadiene

(2-((trimethylsilyl)methyl)cyclopropyl)methanol Structure

116264-56-3

(2-((trimethyls...

~%

octa-4,7-dien-1-ol Structure

81651-45-8

octa-4,7-dien-1-ol

2-((trimethylsilyl)methyl)cyclopropanecarbaldehyde Structure

116264-58-5

2-((trimethylsi...

~%

octa-4,7-dien-1-ol Structure

81651-45-8

octa-4,7-dien-1-ol

N/A Structure

943-92-0

N/A

~%

octa-4,7-dien-1-ol Structure

81651-45-8

octa-4,7-dien-1-ol

(S)-4-((tert-butyldimethylsilyl)oxy)-1-((1R,2R)-2-((trimethylsilyl)methyl)cyclopropyl)butan-1-ol Structure

116264-61-0

(S)-4-((tert-bu...

~%

octa-4,7-dien-1-ol Structure

81651-45-8

octa-4,7-dien-1-ol


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