Synthesis of anthracyclinones by electrophilic and nucleophilic addition to anthraquinones
1990; Elsevier BV; Volume: 46; Issue: 2 Linguagem: Inglês
10.1016/s0040-4020(01)85414-4
ISSN1464-5416
Autores Tópico(s)Oxidative Organic Chemistry Reactions
ResumoDiels-Alder reactions have predominated in the condensation of different fragments in the synthesis of daunomycinone type anthracyclinones. The best methods discovered only recently for the preparation of optically active rhodomycinones involve the incorporation of chiral aldehydes using the Marschalk reaction with anthraquinones. The Marschalk reaction also proved very useful in the preparation of anthraquinone ketoesters which are excellent precursors for racemic anthracyclinones with an ester group at C-10. The nucleophilic additions to anthraquinones have introduced, preparatively and also mechanistically, interesting new aspects into anthraquinone chemistry
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