Abstract
A highly regioselective Diels-Alder approach toward the bioactive natural products hygrocin B and divergolide C is presented. The route uses an unusual benzoquinone-azepinone dienophile prepared in 8 steps from ethyl 8-methoxy-1-naphthoate, by a route which includes, as key steps, a Birch alkylation and a Beckmann rearrangement of a tetralone oxime, both of which are demonstrated on multigram scale. The naphthoquinone-azepinone core is suitably functionalized for addition of the ansa-chain, found in the natural products.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Alkylation
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Azepines / chemical synthesis*
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Azepines / chemistry
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Benzoquinones / chemistry*
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Biological Products / chemical synthesis*
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Biological Products / chemistry
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Lactams, Macrocyclic / chemical synthesis*
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Lactams, Macrocyclic / chemistry
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Macrolides / chemical synthesis*
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Macrolides / chemistry
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Molecular Structure
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Naphthoquinones / chemical synthesis*
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Naphthoquinones / chemistry
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Oximes / chemistry
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Stereoisomerism
Substances
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Azepines
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Benzoquinones
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Biological Products
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Lactams, Macrocyclic
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Macrolides
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Naphthoquinones
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Oximes
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divergolide C
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hygrocin B