Metrics
1 Record Views
Journal article
Programmed Polyene Cyclization Enabled by Chromophore Disruption
Journal of the American Chemical Society, Vol.144(14), pp.6193-6199
04/13/2022
PMCID: PMC10559755
PMID: 35377634
Web of Science ID: WOS:000790698300011
Abstract
A new polyene cyclization strategy exploiting β-ionyl derivatives was developed. Photoinduced deconjugation of the extended π-system within these chromophores unveils a contrathermodynamic polyene that engages in a Heck bicyclization to afford [4.4.1]-propellanes. This cascade improves upon the limited regioselectivity achieved using existing biomimetic tactics and tolerates both electron-rich and electron-deficient (hetero)aryl groups. The utility of this approach was demonstrated with the diverted total synthesis of taxodione and salviasperanol, two isomeric abietane diterpenes that were previously inaccessible along the same synthetic pathway.
Related links
Details
- Title
- Programmed Polyene Cyclization Enabled by Chromophore Disruption
- Publication Details
- Journal of the American Chemical Society, Vol.144(14), pp.6193-6199
- Resource Type
- Journal article
- Publisher
- American Chemical Society
- Number of pages
- 7
- Grant note
- R01GM125926 / NIGMS branch of the NIH CRC-3425 / Florida State University (FSU) Planning Grant
- Copyright
- © 2022 American Chemical Society
- Identifiers
- WOS:000790698300011; 99381856817606600
- Academic Unit
- Chemistry; Hal Marcus College of Science and Engineering
- Language
- English