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Construction of the [6,5,7,5] Tetracyclic Core of Calyciphylline A Type Alkaloids via a Tandem Semipinacol Rearrangement/Nicholas Reaction.
- Source :
-
Organic Letters . Sep2017, Vol. 19 Issue 17, p4648-4651. 4p. - Publication Year :
- 2017
-
Abstract
- A novel and efficient approach toward the assembly of the synthetically challenging tetracyclic [6,5,7,5] core structure of calyciphylline A-type alkaloids is developed. The synthetic route features a tandem semipinacol rearrangement/Nicholas reaction that has been devised strategically to construct the spirocyclic A/B ring and the sterically congested vicinal all-carbon quaternary carbon centers in high diastereoselectivity. Late-stage installation of the hydropyrrole ring and the strained 7-membered ring via a double-reductive amination and ring-closing metathesis, respectively, has also been realized. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 15237060
- Volume :
- 19
- Issue :
- 17
- Database :
- Academic Search Index
- Journal :
- Organic Letters
- Publication Type :
- Academic Journal
- Accession number :
- 124966678
- Full Text :
- https://doi.org/10.1021/acs.orglett.7b02274