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

The chemistry of thujone. XVI. Versatile and efficient routes to safronitrile, β-cyclogeranonitrile, β-cyclocitral, damascones, and their analogues

…, PJ Gunning, RG Clewley, J Somerville…

Index: Kutney, James P.; Gunning, Philip J.; Clewley, Robin G.; Somerville, John; Rettig, Steven J. Canadian Journal of Chemistry, 1992 , vol. 70, # 7 p. 2094 - 2114

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Citation Number: 7

Abstract

Thujone, a waste by-product of the Canadian forest industry, has been utilized as a starting material to develop a versatile synthetic route to the damascones (rose oil ketones) and related analogues. The synthetic sequence provides a route to β-cyclocitral (45), the latter having been previously converted to β-damascone (2). In addition, thujone-derived intermediates are converted to β-damascenone (48) and to intermediates that can be ...

2,5-dimethylcyclohexanone Structure

2,5-dimethylcyc...

methyl iodide Structure

~%

2,2,6-trimethylcyclohexanone Structure

2,2,6-trimethyl...

2,2,6,6-TETRAMETHYLCYCLOHEXANONE Structure

2,2,6,6-TETRAME...

N/A Structure

~27%

2,6,6-Trimethylcyclohexa-1,3-dien-1-ylcarbonitrile Structure

2,6,6-Trimethyl...

(1S,5S) 4,4-Dimethyl-1-(1-methylethyl)-bicyclo[3.1.0]hexan-3-one Structure

(1S,5S) 4,4-Dim...

~%

2,6,6-Trimethylcyclohexa-1,3-dien-1-ylcarbonitrile Structure

2,6,6-Trimethyl...

2,2,6-trimethylcyclohexanone Structure

2,2,6-trimethyl...

~%

2,6,6-Trimethylcyclohexa-1,3-dien-1-ylcarbonitrile Structure

2,6,6-Trimethyl...

1-hydroxy-2,2,6-trimethyl-cyclohexanecarbonitrile Structure

1-hydroxy-2,2,6...

~%

2,6,6-Trimethylcyclohexa-1,3-dien-1-ylcarbonitrile Structure

2,6,6-Trimethyl...

2,4,4-Trimethylcyclohex-2-en-1-one-3-carbonitrile Structure

2,4,4-Trimethyl...

~%

2,6,6-Trimethylcyclohexa-1,3-dien-1-ylcarbonitrile Structure

2,6,6-Trimethyl...

1-isopropyl-2,4,4-trimethyl-bicyclo[3.1.0]hexan-3-one Structure

1-isopropyl-2,4...

~%

2,6,6-Trimethylcyclohexa-1,3-dien-1-ylcarbonitrile Structure

2,6,6-Trimethyl...

1-isopropyl-2,4,4-trimethyl-bicyclo[3.1.0]hexan-3-one Structure

1-isopropyl-2,4...

~%

2,6,6-Trimethylcyclohexa-1,3-dien-1-ylcarbonitrile Structure

2,6,6-Trimethyl...

2,6,6-trimethylcyclohexene-1-carbonitrile Structure

2,6,6-trimethyl...

~91%

β-Cyclocitral Structure

N/A Structure

~%

β-Cyclocitral Structure

1-hydroxy-2,2,6-trimethyl-cyclohexanecarbonitrile Structure

1-hydroxy-2,2,6...

~%

β-Cyclocitral Structure

(1S,5S) 4,4-Dimethyl-1-(1-methylethyl)-bicyclo[3.1.0]hexan-3-one Structure

(1S,5S) 4,4-Dim...

~%

β-Cyclocitral Structure

2,2,6-trimethylcyclohexanone Structure

2,2,6-trimethyl...

~%

β-Cyclocitral Structure

2,4,4-Trimethylcyclohex-2-en-1-one-3-carbonitrile Structure

2,4,4-Trimethyl...

~%

β-Cyclocitral Structure

3-Hydroxy-2,6,6-trimethyl-1-cyclohexene-1-carbonitrile Structure

3-Hydroxy-2,6,6...

~%

β-Cyclocitral Structure

1-isopropyl-2,4,4-trimethyl-bicyclo[3.1.0]hexan-3-one Structure

1-isopropyl-2,4...

~%

β-Cyclocitral Structure

1-isopropyl-2,4,4-trimethyl-bicyclo[3.1.0]hexan-3-one Structure

1-isopropyl-2,4...

~%

β-Cyclocitral Structure

(1S,5S) 4,4-Dimethyl-1-(1-methylethyl)-bicyclo[3.1.0]hexan-3-one Structure

(1S,5S) 4,4-Dim...

~%

α-Cyclogeranonitrile Structure

α-Cyclogeranonitrile

2,2,6-trimethylcyclohexanone Structure

2,2,6-trimethyl...

~%

α-Cyclogeranonitrile Structure

α-Cyclogeranonitrile

2,6,6-trimethylcyclohexene-1-carbonitrile Structure

2,6,6-trimethyl...

~%

α-Cyclogeranonitrile Structure

α-Cyclogeranonitrile

2,4,4-Trimethylcyclohex-2-en-1-one-3-carbonitrile Structure

2,4,4-Trimethyl...

~%

α-Cyclogeranonitrile Structure

α-Cyclogeranonitrile

1-hydroxy-2,2,6-trimethyl-cyclohexanecarbonitrile Structure

1-hydroxy-2,2,6...

~%

α-Cyclogeranonitrile Structure

α-Cyclogeranonitrile

3-Hydroxy-2,6,6-trimethyl-1-cyclohexene-1-carbonitrile Structure

3-Hydroxy-2,6,6...

~%

α-Cyclogeranonitrile Structure

α-Cyclogeranonitrile

1-isopropyl-2,4,4-trimethyl-bicyclo[3.1.0]hexan-3-one Structure

1-isopropyl-2,4...

~%

α-Cyclogeranonitrile Structure

α-Cyclogeranonitrile

1-isopropyl-2,4,4-trimethyl-bicyclo[3.1.0]hexan-3-one Structure

1-isopropyl-2,4...

~%

α-Cyclogeranonitrile Structure

α-Cyclogeranonitrile

N/A Structure

~%

2,6,6-trimethylcyclohexene-1-carbonitrile Structure

2,6,6-trimethyl...

α-Cyclogeranonitrile Structure

α-Cyclogeranonitrile

(E)-1-(2,6,6-Trimethylcyclohexa-1,3-dienyl)but-2-en-1-ol Structure

(E)-1-(2,6,6-Tr...

~99%

1-(2,6,6-TRIMETHYLCYCLOHEXA-1,3-DIEN-1-YL)BUT-2-EN-1-ONE Structure

1-(2,6,6-TRIMET...

Alkylation of enolates with triflates

[Bates, Robert B.; Taylor, Stuart R. Journal of Organic Chemistry, 1993 , vol. 58, # 16 p. 4469 - 4470]

Bibliographie normande 1981

[Haller; Cornubert Bulletin de la Societe Chimique de France, 1927 , vol. <4> 41, p. 367]

Bibliographie normande 1981

[Haller; Cornubert Bulletin de la Societe Chimique de France, 1927 , vol. <4> 41, p. 367]

Bibliographie normande 1981

[Haller; Cornubert Bulletin de la Societe Chimique de France, 1927 , vol. <4> 41, p. 367]

Bibliographie normande 1981

[Haller; Cornubert Bulletin de la Societe Chimique de France, 1927 , vol. <4> 41, p. 367]