Abstract
The first asymmetric total synthesis of (+)-conicol has been achieved via a key step reaction involving the organocatalytic domino oxa-Michael-Michael-Michael-aldol condensation of 2-((E)-2-nitrovinyl)benzene-1,4-diol and alpha,beta-unsaturated aldehydes. Structures of the three-component domino reaction adducts, 20 and 21, including their absolute configurations, were confirmed unambiguously by X-ray analysis. Through this work, the absolute configuration of (+)-conicol was thereby elucidated.
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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Animals
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Antineoplastic Agents / chemical synthesis*
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Antineoplastic Agents / chemistry
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Antineoplastic Agents / pharmacology
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Catalysis
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Crystallography, X-Ray
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Drug Screening Assays, Antitumor
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Haplorhini
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Humans
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Marine Biology
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Molecular Conformation
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Molecular Structure
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Stereoisomerism
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Terpenes / chemical synthesis*
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Terpenes / chemistry
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Terpenes / pharmacology
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Urochordata / chemistry
Substances
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Aldehydes
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Antineoplastic Agents
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Terpenes
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conicol