Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
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
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Keywords: cycloshikonin, O-silyl ketene acetal, naphthazarin, naphthodiquinone, Michael reaction, sigmatropic rearrangement
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1993 Volume 41 Issue 9 Pages 1549-1556

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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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© The Pharmaceutical Society of Japan
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