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Design and Synthesis of Estrarubicin: a Novel Class of Estrogen‐Anthracenedione Hybrids
Author(s) -
De Riccardis Francesco,
Meo Daniela,
Izzo Irene,
Di Filippo Marcello,
Casapullo Agostino
Publication year - 1998
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(199809)1998:9<1965::aid-ejoc1965>3.0.co;2-s
Subject(s) - chemistry , cycloaddition , moiety , stereoselectivity , diene , enone , selectivity , epoxide , anthraquinone , estrone , stereochemistry , diels–alder reaction , combinatorial chemistry , organic chemistry , biochemistry , natural rubber , hormone , catalysis
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 LiClO 4 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 Δ 17(20) bond yielded estrarubicin 2 .