Progress toward the total synthesis of dihydrolycolucine and related "miscellaneous" Lycopodium alkaloids

ORGN 745

Alakesh Bisai and Richmond Sarpong. Department of Chemistry, University of California, Berkeley, 836 Latimer Hall, Berkeley, CA 94720
Dihydrolycolucine (1) and its congeners are C30N3 type Lycopodium alkaloids. These alkaloids were isolated by Ayer and co-workers in 1979 from Lycopodium lucidulum. They were assumed to originate from the phlegmarine skeleton (7). Recently, our group completed the total synthesis of lyconadin A (5) from the tetracyclic intermediate (8). We are currently extending our strategy to the synthesis of other Lycopodium alkaloids such as dihydrolycolucine (1). Our strategy to dihydrolycolucine (1) exploits the coupling of tetracyclic phosphonate (9) and bicyclic ketone (10) via a Horner-Wadsworth-Emmons reaction.