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

Australian Journal of Chemistry

Chemical studies of the Proteaceae. IX. Synthesis of 5-alkylresorcinols from aliphatic precursors

L Cleaver, JA Croft, E Ritchie, WC Taylor

Index: Cleaver,L. et al. Australian Journal of Chemistry, 1976 , vol. 29, p. 1989 - 2001

Full Text: HTML

Citation Number: 19

Abstract

Abstract Methods for the aromatization of ethyl 6-alkyl-2, 4-dioxocyclohexanecarboxylates, available from the base-catalysed condensation between α, β-unsaturated esters and acetoacetic ester, and related substances have been explored. 5-Nonyl-and 5-tridecyl- resorcinol (grevillol) have been synthesized by this route but it is not suitable for the synthesis of 5-alkenylresorcinols or substances of the striatol type.

Ethyl dodec-2-enoate Structure

Ethyl dodec-2-enoate

~%

2-methyl-5-nonylcyclohexane-1,3-dione Structure

2-methyl-5-nony...

ethyl 2-nonyl-4,6-dioxocyclohexane-1-carboxylate Structure

ethyl 2-nonyl-4...

~%

2-methyl-5-nonylcyclohexane-1,3-dione Structure

2-methyl-5-nony...

5-nonylcyclohexane-1,3-dione Structure

5-nonylcyclohex...

methyl iodide Structure

~%

2-methyl-5-nonylcyclohexane-1,3-dione Structure

2-methyl-5-nony...

3-Brom-2-hydroxy-4-methoxy-6-methylbenzoesaeureethylester Structure

3-Brom-2-hydrox...

~%

Ethyl everninate Structure

Ethyl everninate

Ethyl dodec-2-enoate Structure

Ethyl dodec-2-enoate

~%

4,6-dibromo-2-methyl-5-nonylbenzene-1,3-diol Structure

4,6-dibromo-2-m...

5-nonylcyclohexane-1,3-dione Structure

5-nonylcyclohex...

~%

4,6-dibromo-2-methyl-5-nonylbenzene-1,3-diol Structure

4,6-dibromo-2-m...

ethyl 2-nonyl-4,6-dioxocyclohexane-1-carboxylate Structure

ethyl 2-nonyl-4...

~%

4,6-dibromo-2-methyl-5-nonylbenzene-1,3-diol Structure

4,6-dibromo-2-m...

2-methyl-5-nonylcyclohexane-1,3-dione Structure

2-methyl-5-nony...

~%

4,6-dibromo-2-methyl-5-nonylbenzene-1,3-diol Structure

4,6-dibromo-2-m...

diazomethane Structure

5-Methyl-1,3-cyclohexanedione Structure

5-Methyl-1,3-cy...

~%

3-methoxy-5-methylcyclohex-2-en-1-one Structure

3-methoxy-5-met...

Ethyl dodec-2-enoate Structure

Ethyl dodec-2-enoate

~%

2-methyl-5-nonylbenzene-1,3-diol Structure

2-methyl-5-nony...

5-nonylcyclohexane-1,3-dione Structure

5-nonylcyclohex...

~%

2-methyl-5-nonylbenzene-1,3-diol Structure

2-methyl-5-nony...

ethyl 2-nonyl-4,6-dioxocyclohexane-1-carboxylate Structure

ethyl 2-nonyl-4...

~%

2-methyl-5-nonylbenzene-1,3-diol Structure

2-methyl-5-nony...

4,6-dibromo-2-methyl-5-nonylbenzene-1,3-diol Structure

4,6-dibromo-2-m...

~%

2-methyl-5-nonylbenzene-1,3-diol Structure

2-methyl-5-nony...

2-methyl-5-nonylcyclohexane-1,3-dione Structure

2-methyl-5-nony...

~%

2-methyl-5-nonylbenzene-1,3-diol Structure

2-methyl-5-nony...

Ethyl dodec-2-enoate Structure

Ethyl dodec-2-enoate

~%

acetic acid,2-methyl-5-nonylbenzene-1,3-diol Structure

acetic acid,2-m...

5-nonylcyclohexane-1,3-dione Structure

5-nonylcyclohex...

~%

acetic acid,2-methyl-5-nonylbenzene-1,3-diol Structure

acetic acid,2-m...

ethyl 2-nonyl-4,6-dioxocyclohexane-1-carboxylate Structure

ethyl 2-nonyl-4...

~%

acetic acid,2-methyl-5-nonylbenzene-1,3-diol Structure

acetic acid,2-m...

2-methyl-5-nonylcyclohexane-1,3-dione Structure

2-methyl-5-nony...

Ethanoic anhydride Structure

Ethanoic anhydride

~%

acetic acid,2-methyl-5-nonylbenzene-1,3-diol Structure

acetic acid,2-m...

2,5-Dimethylcyclohexane-1,3-dione Structure

2,5-Dimethylcyc...

~%

4,6-dibromo-2,5-dimethylbenzene-1,3-diol Structure

4,6-dibromo-2,5...

Ethyl dodec-2-enoate Structure

Ethyl dodec-2-enoate

Ethyl acetoacetate Structure

Ethyl acetoacetate

~%

ethyl 2-nonyl-4,6-dioxocyclohexane-1-carboxylate Structure

ethyl 2-nonyl-4...

tetradecanal Structure

~%

ethyl 2,4-dioxo-6-tridecylcyclohexane-1-carboxylate Structure

ethyl 2,4-dioxo...

Ethanol Structure

Hexadecenoic acid Structure

Hexadecenoic acid

Ethyl acetoacetate Structure

Ethyl acetoacetate

~%

ethyl 2,4-dioxo-6-tridecylcyclohexane-1-carboxylate Structure

ethyl 2,4-dioxo...

ethyl 2,4-dioxo-6-tridecylcyclohexane-1-carboxylate Structure

ethyl 2,4-dioxo...

~%

ethyl 3,5-dibromo-2,4-dihydroxy-6-tridecylbenzoate Structure

ethyl 3,5-dibro...

5-Methyl-1,3-cyclohexanedione Structure

5-Methyl-1,3-cy...

~%

RESORCINOL44METHYLENEBIS6CHLORO Structure

RESORCINOL44MET...

ethyl 3,5-dibromo-2,4-dihydroxy-6-tridecylbenzoate Structure

ethyl 3,5-dibro...

~%

grevillol Structure

ethyl 2,4-dihydroxy-6-tridecylbenzoate Structure

ethyl 2,4-dihyd...

~%

grevillol Structure

ethyl 2-nonyl-4,6-dioxocyclohexane-1-carboxylate Structure

ethyl 2-nonyl-4...

~%

ethyl 3,5-dibromo-2,4-dihydroxy-6-nonylbenzoate Structure

ethyl 3,5-dibro...

ethyl 3,5-dibromo-2,4-dihydroxy-6-tridecylbenzoate Structure

ethyl 3,5-dibro...

~%

ethyl 2,4-dihydroxy-6-tridecylbenzoate Structure

ethyl 2,4-dihyd...

Malonic acid Structure

tetradecanal Structure

~%

Hexadecenoic acid Structure

Hexadecenoic acid

ethyl 3,5-dibromo-2,4-dihydroxy-6-nonylbenzoate Structure

ethyl 3,5-dibro...

~%

ethyl 2,4-dihydroxy-6-nonylbenzoate Structure

ethyl 2,4-dihyd...

1,12-bis-diazo-dodecane-2,11-dione Structure

1,12-bis-diazo-...

~%

1,1,12,12-tetrabromododecane-2,11-dione Structure

1,1,12,12-tetra...

1,12-bis-diazo-dodecane-2,11-dione Structure

1,12-bis-diazo-...

~%

5-[6-(3,5-dioxocyclohexyl)hexyl]cyclohexane-1,3-dione Structure

5-[6-(3,5-dioxo...

1,1,12,12-tetrabromododecane-2,11-dione Structure

1,1,12,12-tetra...

~%

5-[6-(3,5-dioxocyclohexyl)hexyl]cyclohexane-1,3-dione Structure

5-[6-(3,5-dioxo...

cis,cis-Dodeca-2,10-dien-1,12-dicarbonsaeuredimethylester Structure

cis,cis-Dodeca-...

Ethyl acetoacetate Structure

Ethyl acetoacetate

~%

5-[6-(3,5-dioxocyclohexyl)hexyl]cyclohexane-1,3-dione Structure

5-[6-(3,5-dioxo...

Ethyl dodec-2-enoate Structure

Ethyl dodec-2-enoate

~%

5-nonylcyclohexane-1,3-dione Structure

5-nonylcyclohex...

ethyl 2-nonyl-4,6-dioxocyclohexane-1-carboxylate Structure

ethyl 2-nonyl-4...

~%

5-nonylcyclohexane-1,3-dione Structure

5-nonylcyclohex...

Ethyl dodec-2-enoate Structure

Ethyl dodec-2-enoate

~%

2,4,6-tribromo-5-nonylbenzene-1,3-diol Structure

2,4,6-tribromo-...

5-nonylcyclohexane-1,3-dione Structure

5-nonylcyclohex...

~%

2,4,6-tribromo-5-nonylbenzene-1,3-diol Structure

2,4,6-tribromo-...

ethyl 2-nonyl-4,6-dioxocyclohexane-1-carboxylate Structure

ethyl 2-nonyl-4...

~%

2,4,6-tribromo-5-nonylbenzene-1,3-diol Structure

2,4,6-tribromo-...

5-[6-(3,5-dioxocyclohexyl)hexyl]cyclohexane-1,3-dione Structure

5-[6-(3,5-dioxo...

Ethanoic anhydride Structure

Ethanoic anhydride

~%

acetic acid,5-[6-(3,5-dihydroxyphenyl)hexyl]benzene-1,3-diol Structure

acetic acid,5-[...