Journal of Organic Chemistry p. 3766 - 3771 (1984)
Update date:2022-08-17
Topics:
Krohn, Karsten
Broser, Erwin
An improved regioselective synthesis for the anthracyclinone precursor 12 is reported using a combination of Diels-Alder and Marschalk reactions.The solvolysis of the benzylic bromides 19/20 with water mainly yields the 7,9-trans-diol 8-demethoxyaranciamycinone (22) whereas the treatment with sodium hydroxide affords the 7,9-cis-diol 21.The α-L-daunosamine glycosides 27-30 are prepared and their absolute configurations are determined by 1H NMR spectroscopy.
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