74827-80-8

Upstream product

• 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 
• 62209-66-9 1,4,9,10-tetrahydro-5,8-dihydroxy-1-methoxy-9,10-dioxo-1,4-ethanoanthracene 
• 4457-32-3 4-nitrobenzyl chloroformate 
• 74827-78-4 p-nitrocarbobenzoxy naphthazarin 
• 475-38-7 5,8-Dihydroxy-1,4-naphthoquinone 
• 2161-90-2 1-methoxy-1,3-cyclohexadiene 
• 62209-65-8 1,4,4a,9a-Tetrahydro-5,8-dihydroxy-1-methoxy-1,4-ethano-9,10-anthrachinon 

Downstream Products

• 21794-55-8 (+/-)-7-epi-daunomycinone 
• 88876-12-4 1,4,6a,9,10,10a-hexahydro-10,12-dihydroxy-1-methoxy-6,8,11(7H)-trioxo-1,4-ethanonaphthacen-5-yl(4-nitrophenyl)methyl carbonate 
• 151694-52-9 (4-nitrophenyl)methyl-1,4,6,6a,7,8,9,10,10a,11-decahydro-10-(1,1-dimethylethoxy)-12-hydroxy-1-methoxy-6,8,11(7H)-trioxo-1,4-ethanonaphthacen-5-yl-carbonate 
• 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

A practical and efficient multigram approach to daunomycinone and derivatives

(+/-)-Daunomycinone and (+/-)-4-demethoxydaunomycinone have been synthesized via two successive Diels-Alder reactions from naphthazarin. Key steps for the construction of the A-ring of the anthracyclinone are the Diels-Alder reaction of the BCD fragments

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).