136949-09-2Relevant articles and documents
Studies Related to Anthracyclines. Part 3. Stereoselective Synthesis of (+)-Daunomycinone
Edwards, W. David,Gupta, Ramesh C.,Raynor, Clive M.,Stoodley, Richard J.
, p. 1913 - 1918 (2007/10/02)
The title compound 2b was prepared by a seven-step sequence from (+/-)-4a,9a-epoxy-4a,9a-dihydro-5-methoxyanthracene-1,4,9,10-tetraone 3b/3c and (E)-1-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyloxy)-3-trimethylsilyloxybuta-1,3-diene 4.Acidic hydrolysis of the crude Diels-Alder cycloadducts of compounds 3b/3c and 4 led, after fractional crystallisation, to the isolation of (5aS,6aR,7S,10aR,11aR)-5a,11a-epoxy-4-methoxy-5a,6a,7,8,9,10,10a,11a-octahydro-7-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyloxy)naphthacene-5,6,9,11,12-pentaone 6b.The last-cited compound was transformed into (+)-daunomycinone 2b by reduction, ethynylation, oxida tion, hydrolysis and hydration steps.