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Communication | Special issue | Vol 13, No. 1, 1979, pp.281-288
Published online, 1st January, 1970
DOI: 10.3987/S-1979-01-0281
Synthesis of 10-Methoxydaunorubicins and of 10(R)-Methoxydoxorubicin via Opening of an Oxirane Intermediate

Sergio Penco,* Fausto Gozzi, Aristide Vigevani, Marzia Ballabio, and Federico Arcamone

*Farmitalia Carlo Erba S.p.A, Ricerca & Sviluppo Chimico, Via dei Gracchi,35 20146 Milan, Italy

Abstract

Epoxidation of 9,10-anhydro-13-dihydro-N-trifluoroacetyldaunorubicin provides stereoselectively the corresponding α oxirane derivative. Opening of the intermediate by methanol affords 10(R)- and 10(S)-methoxydaunorubicins. From 1H n.m.r. studies it appears that the conformation of ring A of 10(S)-derivative has changed to half-boat. The preliminary biological data of these analogs, as well as of 10(R)-methoxydoxorubicin are reported.