10-Hydroxy Lycopodium alkaloids
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]
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.
Synthesis
The first enantioselective synthesis of 10-hydroxylycopodine, deacetylpaniculine and paniculine was published by Mrinmoy Saha and Professor Rich Carter in 2013 from Oregon State University. A common intermediate strategy was used to accomplish the total syntheses.[3] The key steps toward the syntheses are an organocatalyzed (Proline sulfonamide catalyst nicknamed as Hua Cat.) Michael reaction and a Zn (OTf)2 mediated conformationally accelerated Mannich reaction.
