Kou, Kevin G. M., Pflueger, Jason J, Kiho, Toshihiro, Morrill, Louis C. ORCID: https://orcid.org/0000-0002-6453-7531, Fisher, Ethan L., Clagg, Kyle, Lebold, Terry P, Kisunzu, Jessica K and Sarpong, Richmond 2018. A benzyne insertion approach to hetisine-type diterpenoid alkaloids: synthesis of cossonidine (davisine). Journal of the American Chemical Society 140 (26) , pp. 8105-8109. 10.1021/jacs.8b05043 |
Preview |
PDF
- Accepted Post-Print Version
Download (828kB) | Preview |
Abstract
The hetisine-type natural products exhibit one of the most complex carbon skeletons within the diterpenoid alkaloid family. The use of network analysis has enabled a synthesis strategy to access alkaloids in this class with hydroxylation on the A-ring. Key transformations include a benzyne acyl-alkylation to construct a key fused 6-7-6 tricycle, a chemoselective nitrile reduction, and sequential C–N bond formations using a reductive cyclization and a photochemical hydroamination to construct an embedded azabicycle. Our strategy should enable access to myriad natural and unnatural products within the hetisine-type.
Item Type: | Article |
---|---|
Date Type: | Publication |
Status: | Published |
Schools: | Chemistry |
Publisher: | American Chemical Society |
ISSN: | 0002-7863 |
Date of First Compliant Deposit: | 18 June 2018 |
Date of Acceptance: | 11 June 2018 |
Last Modified: | 07 Nov 2023 19:41 |
URI: | https://orca.cardiff.ac.uk/id/eprint/112528 |
Citation Data
Cited 49 times in Scopus. View in Scopus. Powered By Scopus® Data
Actions (repository staff only)
Edit Item |