The 10-hydroxy Lycopodium alkaloids, which include 10-hydroxylycopodine, deacetylpaniculine, and paniculine, are a series of natural products isolated from a Chilean club moss Lycopodium confertum. Deacetylpaniculine and paniculine were also isolated from Lycopodium paniculatum.
The Lycopodium alkaloids are of interest due to their biological activity and unique skeletal characteristics, however, many compounds in this class have not been well studied.
Synthesis
The first enantioselective synthesis of 10-hydroxylycopodine, deacetylpaniculine and paniculine was published by Mrinmoy Saha and Rich Carter in 2013. Two key ring-closure steps were accomplished by an organocatalytic Michael reaction and a Lewis acid-catalyzed Mannich reaction. The impact of the C10 stereochemistry on the Michael addition to construct the C7–C12 bond and on the Mannich cyclization have been explored recently.
See also
References
- Muñoz, Orlando M.; Castillo, M.; San Feliciano, A. (January 1990). "High Resolution NMR Studies of Paniculine and Related Lycopodium Compounds". Journal of Natural Products. 53 (1): 200–203. doi:10.1021/np50067a032.
- "Lycopodine and the Lycopodium Alkaloids" (PDF). Archived from the original (PDF) on 2016-03-03. Retrieved 2013-08-11. dead link needs update
- Saha, Mrinmoy; Carter, Rich G. (2024-07-05). "Lycopodium Alkaloids: An Intramolecular Michael Reaction Approach". Synlett (in German). 28 (17): 2212–2229. doi:10.1055/s-0036-1588851. ISSN 0936-5214.
- Saha, Mrinmoy; Carter, Rich G. (February 2013). "Toward a Unified Approach for the Lycopodines: Synthesis of 10-Hydroxylycopodine, Deacetylpaniculine, and Paniculine". Organic Letters. 15 (4): 736–739. doi:10.1021/ol303272w. PMC 3616490. PMID 23384410.
- Saha, Mrinmoy; Li, Xin; Collett, Nathan D.; Carter, Rich G. (June 2016). "Unified Synthesis of 10-Oxygenated Lycopodium Alkaloids: Impact of C10-Stereochemistry on Reactivity". J Org Chem. 81 (14): 5963–5980. doi:10.1021/acs.joc.6b00900. PMID 27353498.