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Design and Synthesis of Estrarubicin: a Novel Class of Estrogen-Anthracenedione Hybrids (1998)

De Riccardis, Francesco ; Meo, Daniela ; Izzo, Irene ; [et al.]

Weinheim : Wiley-Blackwell

Liebigs Annalen 1998 (1998), S. 1965-1970

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ISSN: 1434-193X

Keywords: Cycloadditions ; Quinones ; Hormones ; Antitumor agents ; Hybrid molecules ; Chemistry ; General Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: The synthesis of estrarubicin, a member of a new class of estrogen-anthraquinone hybrids, has been accomplished in an 8-step sequence starting from estrone. The octacyclic carbon skeleton has been elaborated by a Diels-Alder reaction using diene 5 and known epoxy-tetrone 6 as precursors. The cycloaddition reaction, performed in 5 M LiClO4 in diethyl ether, revealed notable diastereofacial selectivity of the diene, leading mainly to cycloadduct 8. Elaboration of the dihydroxyanthraquinone moiety and highly stereoselective epoxidation of the Δ17(20) bond yielded estrarubicin 2.

Type of Medium: Electronic Resource

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