Abstract
A triply convergent total synthesis of vineomycinone B2 methyl ester has been achieved by an approach with a longest linear sequence of 16 steps. The synthesis features the use of silicon tethers as disposable linkers to control the regiochemistry in two tandem Diels-Alder reactions of substituted benzynes and glycosyl furans to provide rapid access to the fully intact anthrarufin core of vineomycinone B2 methyl ester.
Publication types
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Research Support, N.I.H., Extramural
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Research Support, Non-U.S. Gov't
MeSH terms
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Anthraquinones / chemical synthesis*
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Antibiotics, Antineoplastic / chemical synthesis*
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Benzene Derivatives / chemistry*
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Cyclization
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Esters / chemical synthesis*
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Fucose / analogs & derivatives*
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Fucose / chemical synthesis
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Furans / chemistry*
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Glycosides / chemical synthesis*
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Methylation
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Models, Chemical
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Streptomyces / chemistry*
Substances
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Anthraquinones
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Antibiotics, Antineoplastic
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Benzene Derivatives
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Esters
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Furans
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Glycosides
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vineomycinone B2 methyl ester
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Fucose
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vineomycin B2