An enantioselective formal synthesis of 4-demethoxydaunomycin using the catalytic asymmetric ring opening reaction of meso-epoxide with p-anisidine

Akihiro Sekine, Takashi Ohshima, Masakatsu Shibasaki

研究成果: Contribution to journalArticle査読

99 被引用数 (Scopus)

抄録

A catalytic asymmetric formal synthesis of 4-demethoxydaunomycin (3) was achieved using a catalytic asymmetric ring opening reaction of meso-epoxide 9 as a key step. The epoxide opening reaction was promoted by 10 mol% of Pr-(R)-BINOL-Ph3P=O complex to give the β-amino alcohol 11 in 80% yield with 65% enantiomeric excess (ee). Single recrystallization enhanced the enantiomeric purity of the β-amino alcohol 11 to 95% ee. The β-amino alcohol 11 was then converted to the known key intermediate 6 through several steps, including a methylation, Hofmann elimination, an oxymercuration, and addition of an ethynyl group in a highly diastereoselective manner.

本文言語英語
ページ(範囲)75-82
ページ数8
ジャーナルTetrahedron
58
1
DOI
出版ステータス出版済み - 1 1 2002
外部発表はい

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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