Indole Diterpene Synthetic Studies. 2. First-Generation Total Synthesis of (-)-Paspaline

Article abstract of DOI:10.1021/jo00275a035

We record here a full account of the first total synthesis of (-)-paspaline (1), the simplest member of a rapidly growing class of architecturally complex diterpene indole alkaloids, many of which possess potent tremorgenic activity.In terms of sequential annulation, the strategy involves the following operations: DE -> CDE -> CDEF -> ABCDEF.Proceeding in 23 steps from Wieland-Miescher ketone, the synthesis afforded (-)-paspaline (1) in high enantiomeric purity.