10-Hydroxy Lycopodium alkaloids

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The 10-hydroxy Lycopodium alkaloids, 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]

10-hydroxy lycopodium alkaliods.PNG

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[edit]

10-Hydroxylycopodine, Deacetylpaniculine and Paniculine.jpeg

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]

See also[edit]

References[edit]

  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).  dead link needs update
  3. ^ Lycopodium Alkaloids: An Intramolecular Michael Reaction Approach |https://www.thieme-connect.com/products/ejournals/abstract/10.1055/s-0036-1588851
  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 3616490Freely accessible. PMID 23384410. 
  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.