Metrics
1 Record Views
Journal article
Catalytic Asymmetric Synthesis of the Pentacyclic Core of (+)-Citrinadin A
Organic letters, Vol.23(13), pp.4981-4985
07/02/2021
PMID: 34114462
Web of Science ID: WOS:000670661700010
Abstract
The synthesis of the pentacylic core of (+)-cit-rinadin A is described. Our strategy harnesses the power of palladium-catalyzed trimethylenemethane chemistry (Pd-TMM) to form the key spirooxindole motif in a catalytic, asymmetric fashion. Upon the conversion of this spirooxindole to a vinyl epoxide electrophile, the piperidine ring is directly added via a diastereoselective metalation followed by an S(N)2' addition. The final ring of the pentacyclic core is then formed through an intramolecular S(N)2 displacement of the resulting activated alcohol.
Related links
Details
- Title
- Catalytic Asymmetric Synthesis of the Pentacyclic Core of (+)-Citrinadin A
- Publication Details
- Organic letters, Vol.23(13), pp.4981-4985
- Resource Type
- Journal article
- Publisher
- ACS Publications
- Number of pages
- 5
- Grant note
- Tamaki Foundation
- Copyright
- © 2021 American Chemical Society
- Identifiers
- WOS:000670661700010; 99381709174006600
- Academic Unit
- Chemistry; Hal Marcus College of Science and Engineering
- Language
- English