Synthesis of a Potent Rhodomycin, Oxaunomycin, and Its Analogs

Yasuyuki KITA; Hiroshi MAEDA; Masayuki KIRIHARA; Yuji FUJII; Toyokazu NAKAJIMA; Hirofumi YAMAMOTO; Yasumitsu TAMURA; Hiromichi FUJIOKA

doi:10.1248/cpb.40.61

Yasuyuki KITA, Hiroshi MAEDA, Masayuki KIRIHARA, Yuji FUJII, Toyokazu NAKAJIMA, Hirofumi YAMAMOTO, Yasumitsu TAMURA, Hiromichi FUJIOKA

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Keywords: anthracycline antibiotic, oxaunomycin, β-rhodomycinone, regioselective glycosidation, total synthesis

JOURNAL FREE ACCESS

1992 Volume 40 Issue 1 Pages 61-65

DOI https://doi.org/10.1248/cpb.40.61

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Abstract

Oxaunomycin (3) and its regioisomer (6) were synthesized by employing regioselective glycosidations of te C-7 hydroxyl group of 10-O-acetyl-β-rhodomycinone (16) and the C-10 hydroxyl group of the C-7, 9-O phenylboronate (14), respectively, in the presence of trimethylsilyl trifluoromethanesulfonate. Under the Konigs-Knorr conditions, 16 was also glycosidated to provide a fluoro sugar analog (7).

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