Asymmetric synthesis of anthracyclinones: Synthesis of a new chiral AB-synthon, (5R,6R)-6-ethyl-5,6-dihydroxy-5,6,7,8-tetrahydro-1,4-naphthoquinone, and its application for a novel regioselective synthesis of (-)-γ-rhodomycinone

Article abstract of DOI:10.1248/cpb.40.32

A new chiral AB-synthon, (5R,6R)-6-ethyl-5,6-dihydroxy-5,6,7,8-tetrahydro-1,4-naphthoquinone (4), for the synthesis of optically active rhodomycinones was prepared stereoselectively from a (-)-α-hydroxy ketone (6). The coupling reactions of 4 with homophthalic anhydride derivatives (9, 12) proceeded in a regioselective manner to give the tetracyclic compounds 10 and 13, respectively. Compound 10 was converted to (-)-γ-rhodomycinone (3) in a two-step sequence. The optical purity (100% ee) of 3 was unambiguously determined by high performance liquid chromatography analysis using a chiral column.

Full text of DOI:10.1248/cpb.40.32

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