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First asymmetric enantioselective total synthesis of phenanthridine alkaloid, (S)-(+)-asiaticumine and its enantiomer.
- Source :
-
Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry . Nov2019, Vol. 60 Issue 48, pN.PAG-N.PAG. 1p. - Publication Year :
- 2019
-
Abstract
- • The enantioselective total synthesis of (+)-asiaticumine A has been accomplished. • The construction of phenanthridine framework by MW-assisted electrocyclization. • The synthesis of 1,2-dihydroxyethyl moiety by Sharpless asymmetric dihydroxylation. • Its absolute configuration was determined to be S by Mosher's method. In this study, the first asymmetric enantioselective total syntheses of (+)-asiaticumine A (2) and its enantiomer were accomplished through a seven-step sequence using the bond formation between the C4a and N5 positions of the phenanthridine framework based on the microwave-assisted electrocyclization of cyclohexenylbenzaldoxime methyl ether as an aza 6π-hexatriene system followed by the Sharpless asymmetric dihydroxylation as the key step. In addition, the absolute configuration of natural (+)- 2 was determined to be S by Mosher's method. [ABSTRACT FROM AUTHOR]
- Subjects :
- *ASYMMETRIC synthesis
*ALKALOIDS
*RACEMIC mixtures
*METHYL ether
Subjects
Details
- Language :
- English
- ISSN :
- 00404039
- Volume :
- 60
- Issue :
- 48
- Database :
- Academic Search Index
- Journal :
- Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 139627903
- Full Text :
- https://doi.org/10.1016/j.tetlet.2019.151278