Pd-Catalyzed C–H Lactonization for Expedient Synthesis of Biaryl Lactones and Total Synthesis of Cannabinol

A practical Pd(II)/Pd(IV)-catalyzed carboxyl-directed C–H activation/C–O cyclization to construct biaryl lactones has been developed. The synthetic utility of this new reaction was demonstrated in an atom-economical and operationally convenient total synthesis of the natural product cannabinol from...

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Bibliographic Details
Published inOrganic letters Vol. 15; no. 11; pp. 2574 - 2577
Main Authors Li, Yan, Ding, Yan-Jun, Wang, Jian-Yong, Su, Yi-Ming, Wang, Xi-Sheng
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 07.06.2013
Amer Chemical Soc
Subjects
Cannabinol - chemical synthesis
Cannabinol - chemistry
Catalysis
Chemistry
Chemistry, Organic
Cyclization
Hydrogen Bonding
Lactones - chemical synthesis
Lactones - chemistry
Molecular Structure
Palladium - chemistry
Physical Sciences
Science & Technology
Stereoisomerism
C(SP)-H BONDS
PALLADIUM
ACTIVATION
ACIDS
NATURAL-PRODUCTS
ARYLATION
BOND FUNCTIONALIZATION
COPPER
STEREOSELECTIVE TOTAL-SYNTHESIS
ENANTIOSELECTIVE TOTAL-SYNTHESIS
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Summary:A practical Pd(II)/Pd(IV)-catalyzed carboxyl-directed C–H activation/C–O cyclization to construct biaryl lactones has been developed. The synthetic utility of this new reaction was demonstrated in an atom-economical and operationally convenient total synthesis of the natural product cannabinol from commercially available starting materials, with the newly developed method used for two key steps.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol400877q