Fastigiatine, a lycopodium alkaloid with a new ring system

Abstract

Fastigiatine, C 19 H 28 N 2 O, is a minor component of the alkaloids of Lycopodiumfastigiatum R • Br • collected in New Zealand. Its structure and relative configuration have been resolved by an X-ray analysis of the free base. The pentacyclic ring system of fastigiatine has not been previously observed in the Lycopodium family of alkaloids or elsewhere. A proposal is presented for its derivation from the tetracyclic flabellidane ring system that is widely distributed among Lycopodium species. The mass spectrum and the 13 C and 1 H nmr spectra of fastigiatine are discussed.