Formal [3 + 3] Cycloaddition Approach to Chromenes and Chromanes. Concise Total Syntheses of (±)-Rhododaurichromanic Acids A and B and Methyl (±)-Daurichromenic Ester

Total syntheses of (±)-rhododaurichromanic acids A and B and methyl (±)-daurichromenic ester are described here. Despite the complex appearances of these compounds, their syntheses are completed in six steps with a 15% overall yield as a mixture by featuring our formal oxa-[3 + 3] cycloaddition meth...

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Bibliographic Details
Published inOrganic letters Vol. 5; no. 21; pp. 3935 - 3938
Main Authors Kurdyumov, Aleksey V, Hsung, Richard P, Ihlen, Kirsten, Wang, Jiashi
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 16.10.2003
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Chromans - chemical synthesis
Chromans - chemistry
Cyclization
Models, Chemical
Molecular Structure
Physical Sciences
Rhododendron - chemistry
Science & Technology
Stereoisomerism
EPOXIDES
ACID
STRATEGY
ALPHA,BETA-UNSATURATED IMINIUM SALTS
REACTIVITY
4-HYDROXYCOUMARIN
CHEMISTRY
CONDENSATION
ELECTROCYCLIC RING-CLOSURE
DERIVATIVES
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Summary:Total syntheses of (±)-rhododaurichromanic acids A and B and methyl (±)-daurichromenic ester are described here. Despite the complex appearances of these compounds, their syntheses are completed in six steps with a 15% overall yield as a mixture by featuring our formal oxa-[3 + 3] cycloaddition methodology.
Bibliography:Medline
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ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/ol030100k