Abstract
The organocatalytic additions of ascorbic acid to various α,β-unsaturated aldehydes via tandem 1,4-conjugate addition/hemiacetalization/hemiketalization were developed, which provided a rapid entry into the 5-5-5 spirodilactone cores of a family of ascorbylated natural products. Based on the described chemistry, total syntheses of leucodrin, leudrin and the proposed structure of dilaspirolactone were achieved.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Aldehydes / chemistry*
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Ascorbic Acid / chemistry*
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Catalysis
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Crystallography, X-Ray
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Lactones / chemical synthesis*
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Lactones / chemistry
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Models, Molecular
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Molecular Structure
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Spiro Compounds / chemical synthesis*
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Spiro Compounds / chemistry
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Spironolactone / chemical synthesis*
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Spironolactone / chemistry
Substances
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Aldehydes
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Lactones
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Spiro Compounds
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leudrin
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Spironolactone
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leucodrin
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Ascorbic Acid