Tetrahedron

Synthetic anthracyclinones-XXVII anthracyclinones by intramolecular marschalk reaction: Synthesis of the feudomycinones and rhodomycinones

K Krohn, W Priyono

Index: Krohn, Karsten; Priyono, Wahyudi Tetrahedron, 1984 , vol. 40, # 22 p. 4609 - 4616

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Citation Number: 16

Abstract

1, 4, 5-Trihydroxy-9, 10-anthraquinone is transformed regioselectively to the α-hydroxy dichlorides 18-21, which are cyclized to yield predominantely the naturally configurated 9, 10-trans-diols 1, 3, 26, and 27 (80 to 96% de). The monotrifluoroacetates 38-40 derived from the trans-diols are hydroxylated via bromination at C-7 to yield almost exclusively the 7, 9-cis- 9, 10-trans-triols α1-rhodomycinone (4), feudomycinone D (7), and 4-0-methyl-β- ...