10-Hydroxy Lycopodium alkaloids

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.^[1]

The Lycopodium alkaloids are of interest due to their biological activity and unique skeletal characteristics,^[2] however, many compounds in this class have not been well studied.^[3]

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.^[4] 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.^[5]

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.

[Lycopodium-1] 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.

[2] "Lycopodine and the Lycopodium Alkaloids" (PDF). Archived from the original (PDF) on 2016-03-03. Retrieved 2013-08-11. dead link needs update

[3] 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.

[Lycopodines-4] 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.

[10-Hydroxy_Lycopodium_alkaloids-5] 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.

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10-Hydroxy Lycopodium alkaloids

Synthesis

See also

References