Preparation of (.+-.) 4-demethoxy-6 (and-11-)-deoxydaunomycinone

Details Preparation of (.+-.) 4-demethoxy-6 (and-11-)-deoxydaunomycinone Preparation of (.+-.) 4-demethoxy-6 (and-11-)-deoxydaunomycinone

1984-04-11

1986-07-15

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

2603516, 549248, C07C 49423, C07D30789

Patent

active

046005374

ABSTRACT:
(.+-.)4-demethoxy-6(and-11-)-deoxydaunomycinone which are starting materials for anthracycline antitumor antibiotics are prepared by reacting 1,2,3,6-tetrahydrophthalic anhydride with an alcohol of the formula ROH, wherein R is lower alkyl, substituted lower alkyl or aryl to form a monoester, subjecting the monoester to a Friedel-Crafts reaction with acetyl chloride, followed by mild alkaline treatment, to give the corresponding .alpha.,.beta. unsaturated ketone, catalytically reducing same to form the corresponding 4-acetyl-perhydrophthalate reacting the latter with 1,4-dimethoxynaphthalone in the presence of tritluoroacetic anhydride and trifluoroacetic acid to form a mixture of two isomeric compounds, submitting said mixture of isomers to a catalytic reduction of the benzylic carbonyl function, followed by treatment thereof with sulphuric acid at room temperature to afford a mixture of tetracyclic isomers, treating the mixture of tetracyclic isomers with sulphuric acid at 80.degree. C. for one hour to give a 1:1 mixture of the racemic anthracyclinones above mentioned.

REFERENCES:
patent: 4465671 (1984-08-01), Angelucci et al.

Affiliated with

Also associated with

Rating

Preparation of (.+-.) 4-demethoxy-6 (and-11-)-deoxydaunomycinone does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Preparation of (.+-.) 4-demethoxy-6 (and-11-)-deoxydaunomycinone, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Preparation of (.+-.) 4-demethoxy-6 (and-11-)-deoxydaunomycinone will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-1740098