60733-74-6Relevant academic research and scientific papers
AN EFFICIENT SYNTHESIS OF OPTICALLY PURE ANTHRACYCLINONE INTERMEDIATES BY THE NOVEL USE OF MICROBIAL REDUCTION
Terashima, Shiro,Tamoto, Katsumi
, p. 3715 - 3718 (1982)
Reduction of the racemic α-hydroxy ketones((+/-)-3a,b) with fermenting baker's yeast followed by fractional recrystallization and oxidation was found to readily afford optically pure anthracyclinone intermediates((R)(-)-3a,b) and their partially optically active antipodes((S)(+)-3a,b).The useless enantiomers((S)(+)-3a,b) and diastereomeric vicinal-diols((+)-5a,b) could be recycled to (+/-)-3a,b and the achiral ketones(6a,b) by racemization and oxidative cleavage, respectively.
Novel Synthesis of Optically Pure Anthracyclinone Intermediates by the Use of Microbial Asymmetric Reduction with Fermenting Baker's Yeast
Tamoto, Katsumi,Terashima, Shiro
, p. 4328 - 4339 (2007/10/02)
Microbial reduction of the racemic α-hydroxy ketones ((+/-)-3a,b) with fermenting baker's yeast was found to afford diastereomeric mixtures of the vicinal-diols ((-)-4a,b) and ((+)-5a,b) in 90 and 91percent yields, respectively.Separation of these diastereomers was readily accomplished by fractional recrystallization, giving pure (-)-4a,b and mixtures of (-)-4a,b and (+)-5a,b.Oxidation of these samples furnished optically pure anthracyclinone intermediates ((R)-(-)-3a,b) and their partially optically active antipodes ((S)-(+)-3a,b).The undesired enantiomers ((S)-(+)-3a,b) and vicinal-diols((+)-5a,b) could be recycled to (+/-)-3a,b and the prochiral ketones (6a,c) by racemization with p-toluenesulfonic acid and oxidative cleavage with sodium metaperiodate, respectively.Another important optically pure anthracyclinone intermediate ((R)-(-)-3c) was prepared from (R)-(-)-3a,b according to the reported method.Keywords - α-hydroxy ketone; microbial reduction; anthracycline; optically pure anthracyclinone; 4-demethoxyanthracycline; optically pure 4-demethoxyanthracyclinone; baker's yeast; oxidation; racemization; vicinal-diol
