Back to Search
Start Over
Stereoselective Syntheses of all the Possible Stereoisomers of Coronafacic Acid
- Source :
- ChemistryOpen, Vol 9, Iss 10, Pp 1008-1017 (2020), ChemistryOpen
- Publication Year :
- 2020
- Publisher :
- Wiley-VCH, 2020.
-
Abstract
- An efficient and stereoselective syntheses of all the possible stereoisomers of coronafacic acid (CFA) has been developed. The stereochemistries of C3a and C7a were controlled in a diastereoselective Diels‐Alder type cycloaddition using a chiral auxiliary. CFA and 6‐epi‐CFA were synthesized by hydrogenation of a common intermediate. During the synthesis of 6‐epi‐CFA, we established that its cis‐fused configuration is important for the introduction of C4‐C5 double bond by dehydration. This report is the first practical synthesis of both 6‐epi‐CFA, and its enantiomer.
- Subjects :
- chemistry.chemical_classification
Chiral auxiliary
Phytochemistry
Full Paper
Double bond
Stereochemistry
natural products
Coronatine
General Chemistry
Full Papers
complex mixtures
Cycloaddition
lcsh:Chemistry
chemistry.chemical_compound
Coronafacic acid
chemistry
lcsh:QD1-999
phytochemistry
Stereoselectivity
Enantiomer
coronatine
Subjects
Details
- Language :
- English
- ISSN :
- 21911363
- Volume :
- 9
- Issue :
- 10
- Database :
- OpenAIRE
- Journal :
- ChemistryOpen
- Accession number :
- edsair.doi.dedup.....17198d5febaf88c93bfd95d2a4442757