C-Alkylation of Methyl leuco-6-Deoxykermesate by Aldol Reactions and its Application to Synthesis of Carminic Acid

…, KMA Malik, DE Hibbs, MB Hursthouse

Index: Bingham, Steve J.; Tyman, John H. P.; Malik, K. M. A.; Hibbs, David E.; Hursthouse, Michael B. Journal of Chemical Research, Miniprint, 1998 , # 9 p. 2465 - 2496

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Abstract

In a non-aqueous medium in the presence of piperidinium acetate, methyl leuco-6- deoxykermesate reacts in aldol fashion with aldehydes regioselectively to give 6-alkyl products while under aqueous alkaline conditions over a prolonged time, 7-alkyl compounds are selectively formed; the structures of the 6-alkyl series was confirmed by an X- ray crystal structure determination of the 6-methyl member, namely methyl 3, 5, 8- ...

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Formaldehyde Structure

50-00-0

Formaldehyde

1,4-Anthracenedione,2,3-dihydro-9,10-dihydroxy- Structure

17648-03-2

1,4-Anthracened...

~84%

9,10-Anthracenedione,1,4-dihydroxy-2-methyl- Structure

2589-39-1

9,10-Anthracene...

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1,4-dihydroxy-9,10-dioxoanthracene-2-carbaldehyde Structure

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Quinizarin Structure

81-64-1

Quinizarin

~%

1,4-dihydroxy-9,10-dioxoanthracene-2-carbaldehyde Structure

56594-55-9

1,4-dihydroxy-9...

1,4-Anthracenedione,2,3-dihydro-9,10-dihydroxy- Structure

17648-03-2

1,4-Anthracened...

~%

1,4-dihydroxy-9,10-dioxoanthracene-2-carbaldehyde Structure

56594-55-9

1,4-dihydroxy-9...


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