Back to Search
Start Over
Total Synthesis of (+)-Chimonanthine, (+)-Folicanthine, and (−)-Calycanthine.
- Source :
-
Journal of Organic Chemistry . 10/16/2015, Vol. 80 Issue 20, p10309-10316. 8p. - Publication Year :
- 2015
-
Abstract
- Facile, straightforward, and asymmetric total syntheses of (+)-chimonanthine (1), (+)-folicanthine (2), and (−)-calycanthine (3) were accomplished in four to five steps from commercially available tryptamine. The synthesis features copper-mediated asymmetric cyclodimerization of chiral tryptamine derivative, which established a new entry into constructing the sterically hindered vicinal quaternary stereogenic carbon centers of dimeric hexahydropyrroloindole alkaloids in one procedure. An unprecedented base-induced isomerization from the chimonanthine skeleton to the calycanthine skeleton was observed and facilitated the synthesis of (−)-calycanthine (3). [ABSTRACT FROM AUTHOR]
- Subjects :
- *BICYCLIC compounds
*AMIDES
*TRYPTAMINE
*CHEMICAL synthesis
*CHEMICAL derivatives
Subjects
Details
- Language :
- English
- ISSN :
- 00223263
- Volume :
- 80
- Issue :
- 20
- Database :
- Academic Search Index
- Journal :
- Journal of Organic Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 110424910
- Full Text :
- https://doi.org/10.1021/acs.joc.5b01907