Flustra foliacea Flustramines

Marine Alkaloids. 3. Bromo-Substituted Alkaloids from the Marine Bryozoan Flustra foliacea, Flustramine C and Flustraminol A and B. J. Org. Chem. 46, 3440 (1981). 

Flustra foliacea L., a marine bryozoan, or moss animal, contains29 two isomeric metabolites, flustramine A and flustramine B, which are eserine derivatives that contain one bromine and two isoprenyl substituents, at positions 6, 3a, and 8. In... 

The marine bryozoan Flustra foliacea collected in the North Sea has given rise to the isolation of a complicated mixture of alkaloids, twelve of which have so far been identified (32-36). The structures are depicted in Scheme 11 flustramine A (1)... 

Iminium organocatalysis was key to the enantioselective total synthesis of (—)-flustramine B (157) from the marine bryozoan Flustra foliacea by MacMillan and co-workers (Scheme 31) [137], which is discussed here despite not incorporating the entire C5 unit in one step. On treatment of the Boc-protected... 

The discovery of 2-ferf-prenylated deformylflustrabromine (235) as a major metabolite of Flustra foliacea collected near Helgoland [182-184] prompted us to investigate its presumably biomimetic conversion to the pyrrolo[2,3-b]indole flustramine C (236) [185], which is ferf-prenylated at the bridgehead C3a (Scheme 45). For the synthesis of deformylflustrabromine (235), Wb-methyltryptamine (232) was converted to Wb-formyl-Wb-methyltryptamine which cleanly underwent... 

From North Sea Bryozoan Flustra foliacea) several, brominated indole alkaloids have been isolated. These include deformylflustramine and flustramine. Deformylfrustrabromine A and deformylfrustrabromine B... 

Holst, P.B., Anthoni, U., Christophersen, C., and Nielsen, P.H. (1994b) Marine alkaloids, 15. Two alkaloids, flustramine E and debromoflustramine B, from the marine bryozoan Flustra foliacea. J. Nat. Prod., 57, 997-1000. 

---