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

Hiromichi FUJIOKA; Hirofumi YAMAMOTO; Hirokazu ANNOURA; Hiroshi MAEDA; Yasuyuki KITA

doi:10.1248/cpb.40.32

藤岡弘道, 山本博文, 案浦洋一, 前田ひろし, 北泰行

著者情報

キーワード: asymmetric synthesis, (-)-γ-rhodomycinone, rigioselective coupling reaction, chiral AB-synthon, (5R, 6R)-6-ethyl -5, 6-dihydroxy-5, 6, 7, 8-tetrahydro-1, 4-naphthoquinone, CD-synthon, homophthalic anhydride derivative

ジャーナルフリー

1992 年 40 巻 1 号 p. 32-35

DOI https://doi.org/10.1248/cpb.40.32

詳細

抄録

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.

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