10-Hydroxy Lycopodium alkaloids

Class of chemical compounds 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.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 10.1021/np50067a032 center The Lycopodium alkaloids are of interest due to their biological activity and unique skeletal characteristics,Lycopodine and the Lycopodium Alkaloids http://stoltz.caltech.edu/litmtg/mechclub/2008/AHSC7_08.pdf dead https://web.archive.org/web/20160303225242/http://stoltz.caltech.edu/litmtg/mechclub/2008/AHSC7_08.pdf 2016-03-03 2013-08-11 dead link needs update however, many compounds in this class have not been well studied.Saha Mrinmoy Carter Rich G. 2024-07-05 Lycopodium Alkaloids: An Intramolecular Michael Reaction Approach http://www.thieme-connect.de/DOI/DOI?10.1055/s-0036-1588851 Synlett de 28 17 2212–2229 10.1055/s-0036-1588851 0936-5214 subscription Synthesis center|400px 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.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 10.1021/ol303272w 3616490 23384410 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.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 10.1021/acs.joc.6b00900 27353498 See also Lycopodium powder Lycopodium clavatum References Category:Alkaloids