Triquinane sesquiterpenes. An iterative, highly stereocontrolled synthesis of (.+-.)-silphinene

LA Paquette, A Leone-Bay

Index: Paquette,L.A.; Leone-Bay,A. Journal of the American Chemical Society, 1983 , vol. 105, p. 7352

Full Text: HTML

Citation Number: 50

Abstract

Abstract: A total synthesis of (&)-silphinene, a tricyclopentanoid sesquiterpene isolated from the roots of Silphium perfoliatum L., has been achieved. This structurally interesting triquinane was constructed in 15 steps and isolated in efficient overall yield. The key element of the synthesis was the implementation of an iterative cyclopentannulation scheme consisting of twofold conjugate addition of a functionalized organocopper reagent and ...

 Related Synthetic Route
2,2-dimethyl-3-(p-toluensulfonyloxy)propionaldehyde trimethylene acetal Structure

87802-23-1

2,2-dimethyl-3-...

~82%

2-(1-iodo-2-methylpropan-2-yl)-1,3-dioxane Structure

87802-25-3

2-(1-iodo-2-met...

2,2-dimethyl-3-hydroxypropionaldehyde trimethylene acetal Structure

32935-49-2

2,2-dimethyl-3-...

~%

2-(1-iodo-2-methylpropan-2-yl)-1,3-dioxane Structure

87802-25-3

2-(1-iodo-2-met...

2-(2-methylpent-4-en-2-yl)-1,3-dioxolane Structure

87802-43-5

2-(2-methylpent...

~82%

4-(1,3-dioxolan-2-yl)-4-methylpentan-2-one Structure

87802-26-4

4-(1,3-dioxolan...

2,2-Dimethyl-4-pentenal Structure

5497-67-6

2,2-Dimethyl-4-...

~%

4-(1,3-dioxolan-2-yl)-4-methylpentan-2-one Structure

87802-26-4

4-(1,3-dioxolan...

2,2-Dimethyl-4-pentenal Structure

5497-67-6

2,2-Dimethyl-4-...

~%

4-(1,3-dioxan-2-yl)-4-methylpentan-2-one Structure

87802-27-5

4-(1,3-dioxan-2...

2-(2-methylpent-4-en-2-yl)-1,3-dioxolane Structure

87802-43-5

2-(2-methylpent...

~%

2-(1,3-dioxolan-2-yl)-2-methyloct-7-en-4-one Structure

87802-28-6

2-(1,3-dioxolan...

2,2-Dimethyl-4-pentenal Structure

5497-67-6

2,2-Dimethyl-4-...

~%

2-(1,3-dioxolan-2-yl)-2-methyloct-7-en-4-one Structure

87802-28-6

2-(1,3-dioxolan...

4-(1,3-dioxolan-2-yl)-4-methylpentan-2-one Structure

87802-26-4

4-(1,3-dioxolan...

allyl bromide Structure

106-95-6

allyl bromide

~%

2-(1,3-dioxolan-2-yl)-2-methyloct-7-en-4-one Structure

87802-28-6

2-(1,3-dioxolan...

2-(1,3-dioxolan-2-yl)-2-methyloct-7-en-4-one Structure

87802-28-6

2-(1,3-dioxolan...

~80%

7-(1,3-dioxolan-2-yl)-7-methyloctane-2,5-dione Structure

87802-29-7

7-(1,3-dioxolan...

2-(2-methylpent-4-en-2-yl)-1,3-dioxolane Structure

87802-43-5

2-(2-methylpent...

~%

7-(1,3-dioxolan-2-yl)-7-methyloctane-2,5-dione Structure

87802-29-7

7-(1,3-dioxolan...

2,2-Dimethyl-4-pentenal Structure

5497-67-6

2,2-Dimethyl-4-...

~%

7-(1,3-dioxolan-2-yl)-7-methyloctane-2,5-dione Structure

87802-29-7

7-(1,3-dioxolan...

4-(1,3-dioxolan-2-yl)-4-methylpentan-2-one Structure

87802-26-4

4-(1,3-dioxolan...

~%

7-(1,3-dioxolan-2-yl)-7-methyloctane-2,5-dione Structure

87802-29-7

7-(1,3-dioxolan...

2-(2-methylpent-4-en-2-yl)-1,3-dioxolane Structure

87802-43-5

2-(2-methylpent...

~%

2-(1,3-dioxolan-2-yl)-7-ethoxy-2-methyloct-7-en-4-one Structure

87802-30-0

2-(1,3-dioxolan...

2,2-Dimethyl-4-pentenal Structure

5497-67-6

2,2-Dimethyl-4-...

~%

2-(1,3-dioxolan-2-yl)-7-ethoxy-2-methyloct-7-en-4-one Structure

87802-30-0

2-(1,3-dioxolan...

2-ethoxyprop-2-en-1-ol Structure

62861-55-6

2-ethoxyprop-2-...

~%

2-(1,3-dioxolan-2-yl)-7-ethoxy-2-methyloct-7-en-4-one Structure

87802-30-0

2-(1,3-dioxolan...

4-(1,3-dioxolan-2-yl)-4-methylpentan-2-one Structure

87802-26-4

4-(1,3-dioxolan...

2-ethoxyprop-2-en-1-ol,methanesulfonic acid Structure

87802-44-6

2-ethoxyprop-2-...

~%

2-(1,3-dioxolan-2-yl)-7-ethoxy-2-methyloct-7-en-4-one Structure

87802-30-0

2-(1,3-dioxolan...

7-(1,3-dioxolan-2-yl)-7-methyloctane-2,5-dione Structure

87802-29-7

7-(1,3-dioxolan...

~13%

3-[2-(1,3-dioxolan-2-yl)propan-2-yl]-2-methylcyclopent-2-en-1-one Structure

87802-33-3

3-[2-(1,3-dioxo...

3-[2-(1,3-dioxolan-2-yl)-2-methylpropyl]cyclopent-2-en-1-one Structure

87802-31-1

3-[2-(1,3-dioxo...

2-(2-methylpent-4-en-2-yl)-1,3-dioxolane Structure

87802-43-5

2-(2-methylpent...

~%

3-[2-(1,3-dioxolan-2-yl)-2-methylpropyl]cyclopent-2-en-1-one Structure

87802-31-1

3-[2-(1,3-dioxo...

2,2-Dimethyl-4-pentenal Structure

5497-67-6

2,2-Dimethyl-4-...

~%

3-[2-(1,3-dioxolan-2-yl)-2-methylpropyl]cyclopent-2-en-1-one Structure

87802-31-1

3-[2-(1,3-dioxo...

4-(1,3-dioxolan-2-yl)-4-methylpentan-2-one Structure

87802-26-4

4-(1,3-dioxolan...

~%

3-[2-(1,3-dioxolan-2-yl)-2-methylpropyl]cyclopent-2-en-1-one Structure

87802-31-1

3-[2-(1,3-dioxo...

2-(1,3-dioxolan-2-yl)-2-methyloct-7-en-4-one Structure

87802-28-6

2-(1,3-dioxolan...

~%

3-[2-(1,3-dioxolan-2-yl)-2-methylpropyl]cyclopent-2-en-1-one Structure

87802-31-1

3-[2-(1,3-dioxo...

2,2-Dimethyl-4-pentenal Structure

5497-67-6

2,2-Dimethyl-4-...

~%

3-[2-(1,3-dioxan-2-yl)-2-methylpropyl]cyclopent-2-en-1-one Structure

87802-32-2

3-[2-(1,3-dioxa...

4-(1,3-dioxan-2-yl)-4-methylpentan-2-one Structure

87802-27-5

4-(1,3-dioxan-2...

~%

3-[2-(1,3-dioxan-2-yl)-2-methylpropyl]cyclopent-2-en-1-one Structure

87802-32-2

3-[2-(1,3-dioxa...

((Z)-7-[1,3]Dioxan-2-yl-2-ethoxy-7-methyl-5-oxo-oct-1-enyl)-phosphonic acid dimethyl ester Structure

87802-34-4

((Z)-7-[1,3]Dio...

~%

3-[2-(1,3-dioxan-2-yl)-2-methylpropyl]cyclopent-2-en-1-one Structure

87802-32-2

3-[2-(1,3-dioxa...

7-(1,3-dioxolan-2-yl)-7-methyloctane-2,5-dione Structure

87802-29-7

7-(1,3-dioxolan...

~53%

3-[2-(1,3-dioxolan-2-yl)propan-2-yl]-2-methylcyclopent-2-en-1-one Structure

87802-33-3

3-[2-(1,3-dioxo...

3-[2-(1,3-dioxolan-2-yl)-2-methylpropyl]cyclopent-2-en-1-one Structure

87802-31-1

3-[2-(1,3-dioxo...

2-(2-methylpent-4-en-2-yl)-1,3-dioxolane Structure

87802-43-5

2-(2-methylpent...

~%

3-[2-(1,3-dioxolan-2-yl)propan-2-yl]-2-methylcyclopent-2-en-1-one Structure

87802-33-3

3-[2-(1,3-dioxo...

2,2-Dimethyl-4-pentenal Structure

5497-67-6

2,2-Dimethyl-4-...

~%

3-[2-(1,3-dioxolan-2-yl)propan-2-yl]-2-methylcyclopent-2-en-1-one Structure

87802-33-3

3-[2-(1,3-dioxo...

4-(1,3-dioxolan-2-yl)-4-methylpentan-2-one Structure

87802-26-4

4-(1,3-dioxolan...

~%

3-[2-(1,3-dioxolan-2-yl)propan-2-yl]-2-methylcyclopent-2-en-1-one Structure

87802-33-3

3-[2-(1,3-dioxo...

2-(1,3-dioxolan-2-yl)-2-methyloct-7-en-4-one Structure

87802-28-6

2-(1,3-dioxolan...

~%

3-[2-(1,3-dioxolan-2-yl)propan-2-yl]-2-methylcyclopent-2-en-1-one Structure

87802-33-3

3-[2-(1,3-dioxo...

4,4-dimethyl-2-oxocyclopentane-1-carbaldehyde Structure

81887-97-0

4,4-dimethyl-2-...

Ethylene glycol Structure

107-21-1

Ethylene glycol

~77%

2-(1,3-dioxolan-2-yl)-4,4-dimethylcyclopentan-1-one Structure

87802-41-3

2-(1,3-dioxolan...

4,4-Dimethyl-2-cyclopenten-1-one Structure

22748-16-9

4,4-Dimethyl-2-...

~%

2-(1,3-dioxolan-2-yl)-4,4-dimethylcyclopentan-1-one Structure

87802-41-3

2-(1,3-dioxolan...

3,3-dimethylcyclopentan-1-one Structure

20500-49-6

3,3-dimethylcyc...

~%

2-(1,3-dioxolan-2-yl)-4,4-dimethylcyclopentan-1-one Structure

87802-41-3

2-(1,3-dioxolan...

2,2-Dimethyl-4-pentenal Structure

5497-67-6

2,2-Dimethyl-4-...

Ethylene glycol Structure

107-21-1

Ethylene glycol

~99%

2-(2-methylpent-4-en-2-yl)-1,3-dioxolane Structure

87802-43-5

2-(2-methylpent...

2-ethoxyprop-2-en-1-ol Structure

62861-55-6

2-ethoxyprop-2-...

Methanesulfonyl chloride Structure

124-63-0

Methanesulfonyl...

~91%

2-ethoxyprop-2-en-1-ol,methanesulfonic acid Structure

87802-44-6

2-ethoxyprop-2-...

2,2-dimethyl-3-(p-toluensulfonyloxy)propionaldehyde trimethylene acetal Structure

87802-23-1

2,2-dimethyl-3-...

~70%

2-(1-bromo-2-methylpropan-2-yl)-1,3-dioxane Structure

87802-24-2

2-(1-bromo-2-me...

2,2-dimethyl-3-hydroxypropionaldehyde trimethylene acetal Structure

32935-49-2

2,2-dimethyl-3-...

~%

2-(1-bromo-2-methylpropan-2-yl)-1,3-dioxane Structure

87802-24-2

2-(1-bromo-2-me...

3,3-dimethylcyclopentan-1-one Structure

20500-49-6

3,3-dimethylcyc...

Ethyl formate Structure

109-94-4

Ethyl formate

~73%

4,4-dimethyl-2-oxocyclopentane-1-carbaldehyde Structure

81887-97-0

4,4-dimethyl-2-...

4,4-Dimethyl-2-cyclopenten-1-one Structure

22748-16-9

4,4-Dimethyl-2-...

~%

4,4-dimethyl-2-oxocyclopentane-1-carbaldehyde Structure

81887-97-0

4,4-dimethyl-2-...


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