Abstract
Ailanthoidol 1, which can be isolated from Chinese herbal medicine, is achieved in which the longest linear sequence is only six steps in 48% overall yield from commercially available 5-bromo-2-hydroxy-3-methoxybenzaldehyde. The key transformations in the synthesis are the Stille coupling reactions of benzofuranyl bromide with stannanyl compounds. This synthetic strategy can be modified to give access to a variety of different ailanthoidol and XH14 analogues.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Benzaldehydes / chemistry
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Benzofurans / analysis
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Benzofurans / chemical synthesis*
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Catalysis
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Drugs, Chinese Herbal / chemistry
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Guaiacol / analogs & derivatives
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Indicators and Reagents
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Molecular Structure
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Nuclear Magnetic Resonance, Biomolecular
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Stereoisomerism
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Zanthoxylum / chemistry
Substances
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5-bromo-2-hydroxy-3-methoxybenzaldehyde
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Benzaldehydes
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Benzofurans
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Drugs, Chinese Herbal
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Indicators and Reagents
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XH-14
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ailanthoidol
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Guaiacol