Successive Michael Reaction-Sigmatropic Rearrangement of Naphthodiquinone with O-Silylated Ketene Acetals Leading to Synthesis of Cycloshikonin and Structure-Reactivity Relationship for Side Chain of Naphthazarins

Mariko Aso, Ken Kanematsu

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

Synthesis of cycloshikonin via successive Michael reaction-sigmatropic rearrangement of naphthodiquinone with O-silylated ketene acetals is described. The structure dependence of the reactivity of the side chain of intermediary naphthazarin derivatives has also been investigated.

Original languageEnglish
Pages (from-to)1549-1556
Number of pages8
JournalChemical and Pharmaceutical Bulletin
Volume41
Issue number9
DOIs
Publication statusPublished - Jan 1 1993

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Naphthoquinones
Acetals
Derivatives
ketene
naphthazarin

All Science Journal Classification (ASJC) codes

  • Chemistry(all)
  • Drug Discovery

Cite this

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abstract = "Synthesis of cycloshikonin via successive Michael reaction-sigmatropic rearrangement of naphthodiquinone with O-silylated ketene acetals is described. The structure dependence of the reactivity of the side chain of intermediary naphthazarin derivatives has also been investigated.",
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