Lycopodium alkaloids lycopodine class

Isomunchnones play a large part in the synthetic efforts Padwa and co-workers (91-94,96,98,110,111). The Lycopodium alkaloids are a large family of natural products and have inspired numerous synthetic routes to approach these compounds. Interest in this class of alkaloids stems from the myriad of biological properties they exhibit. Padwa utilized the carbonyl ylide methodology in tandem with a cationic 71-cyclization to complete a formal synthesis of ( ) lycopodine (Scheme 4.55) (96,112). 

The first lycopodium alkaloid was isolated from the club moss Lycopodium complanatum by Bodeker as early as 1881 [18] much later its structure was shown to be lycopodine [19]. Since the first comprehensive review on lycopodium alkaloids was published in 1968 [20], new structures have been isolated and the chemistry and biology of this class of compounds have been reviewed several times [6-9, 21], According to Ayer [6], the lycopodium alkaloids are generally considered to comprise of four major classes. Compounds 1-4 are representatives of each group lycopodine 1 (class 1), lycodine 2 (class IT), fawcettimine 3 (class III), and phlegmarine 4 (miscellaneous class IV). 

---