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]
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]
