Abstract
A biomimetic synthesis of zeylanone and zeylanone epoxide, which are natural dimeric naphthoquinones, has been accomplished starting from plumbagin, a natural monomeric naphthoquinone. The key features of our synthesis are cascade intermolecular and intramolecular Michael reactions, followed by epoxidation of the resultant hydroquinone with molecular oxygen.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Biomimetics
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Dimerization
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Epoxy Compounds / chemical synthesis*
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Epoxy Compounds / chemistry
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Hydroquinones / chemistry
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Molecular Structure
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Naphthoquinones / chemical synthesis*
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Naphthoquinones / chemistry
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Vitamin K 3 / chemistry*
Substances
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Epoxy Compounds
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Hydroquinones
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Naphthoquinones
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zeylanone
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Vitamin K 3
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plumbagin