Stereoselective Syntheses of all the Possible Stereoisomers of Coronafacic Acid.
ChemistryOpen
; 9(10): 1008-1017, 2020 10.
Article
em En
| MEDLINE
| ID: mdl-33072470
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.
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MEDLINE
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En
Ano de publicação:
2020
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Article