An Eight‐Step Total Synthesis of Pyrroloquinolone‐Type Lycopodium Alkaloid via a Tandem Annulation Approach †

Summary of main observation and conclusion A total synthesis of 6,7,9,10,12,12 a ‐hexahydro‐2‐methyl‐(2 R ,4 aS ,12 aS )‐2 H ,5 H ‐benzo[ e ]pyrrolo[3,2,1‐ ij ]quinolone‐4,11(1 H ,3 H )‐dione ( 1 ), a unique pyrroloquinolone‐type Lycopodium alkaloid containing a complex 6/6/6/5 tetracyclic core, has been disclosed in eight steps and 38% overall yield. The reported synthesis features a short, efficient synthesis of the crucial multi‐substituted cyclohexanone intermediate with three stereogenic centers, and one‐pot generation of the complex 6/6/6/5 tetracyclic core in a single tandem step.