91740-61-3

Upstream product

• 69387-67-3 11-methyl epidaunomycinone 
• 2161-90-2 1-methoxy-1,3-cyclohexadiene 
• 475-38-7 5,8-Dihydroxy-1,4-naphthoquinone 
• 69986-67-0 5,8-Dihydroxy-4-trimethylsilanyloxy-3,4,4a,9a-tetrahydro-1H-anthracene-2,9,10-trione 
• 69986-68-1 4,5,8-Trihydroxy-3,4,4a,9a-tetrahydro-1H-anthracene-2,9,10-trione 
• 84201-94-5 C₂₅H₂₂O₉ 
• 84201-95-6 C₂₆H₂₄O₈ 
• 84201-96-7 (8S,10R)-8-Acetyl-6,11-diethoxy-10-hydroxy-1-methoxy-7,8,9,10-tetrahydro-naphthacene-5,12-dione 
• 74827-79-5 1,4,4a,9,9a,10-hexahydro-8-hydroxy-1-methoxy-9,10-dioxo-1,4-ethanoanthracen-5-yl(4-nitrophenyl)methyl carbonate 
• 74827-80-8 (4-nitrophenyl)methyl 1,4,9,10-tetrahydro-8-hydroxy-1-methoxy-9,10-dioxo-1,4-ethanoanthracen-5-yl carbonate 
• 88876-13-5 8-ethynyl-1,4,7,8,9,10-hexahydro-5,8,10,12-tetrahydroxy-1-methoxy-1,4-ethanonaphthacene-6,11-dione 
• 74827-83-1 1,4,6a,9,10,10a-hexahydro-5,10,12-trihydroxy-1-methoxy-1,4-ethanonaphthacene-6,8,11(7H)-trione 
• 74827-78-4 p-nitrocarbobenzoxy naphthazarin 
• 74827-82-0 (4-nitrophenyl)methyl 1,4,6,6a,7,10,10a,11-octahydro-12-hydroxy-1-methoxy-6,11-dioxo-8,10-bis(trimethylsilyloxy)-1,4-ethanonaphthacen-5-yl carbonate 

Relevant academic research and scientific papers

AN EFFICIENT, REGIOSPECIFIC SYNTHESIS OF (+/-)-DAUNOMYCINONE

The development of a general strategy for the control of regiochemistry in the Diels-Alder reactions of substituted naphthazarins is described.Application of this strategy to the synthesis of (+/-)-daunomycinone (2) employs two successive regiochemically controlled Diels-Alder reactions and leads to a ten-step, regiospecific synthesis of (+/-)-2 in 36percent overall yield (Scheme 4).

Synthesis of adriamycin and 7,9-epiadriamycin

A process for the synthesis of adriamycin and 7,9-epiadriamycin, both active antineoplastic agents, in which 7-deoxydaunomycinone, in either the 9s or racemic (±) form, is employed as the starting material, the process in one embodiment also being productive of the useful intermediate compound 4-methoxy-6,11-dihydroxy-7,8-dihydro-5,9(10H),12-naphthacenetrione. The process involves converting 7-deoxydaunomicinone successively to daunomycinone, adriamycinone, 14-0-p-anisyldiphenylmethyladriamycinone and finally to adriamycin or to both adriamycin and 7,9-epiadriamycin. When producing the latter mixture of diastereomers, the 7-deoxydaunomycinone starting material is first converted to racemate form by a process involving the successive production of 7-deoxydaunorubicinol, 4-methoxy-6,11-dihydroxy-7,8-dihydro-5,9(10H), 12-naphthacenetrione, (±)-4-methoxy-9-cyano-6,9,11-trihydroxy-7,8,9,10-tetrahydro-5,12-naphthacenedione, (±)-4-methoxy-9-cyano-9-(2'-tetrahydropyranyloxy)-6,11-dihydroxy-7,8,9,10-tetrahydro-5,12-naphthacenedione and (±)-7-deoxydaunomycinone.