Total syntheses of tambjamines C, E, F, G, H, I and J, BE-18591, and a related alkaloid from the marine bacterium Pseudoalteromonas tunicata.
The acetate salts of tambjamines C, E, and F (2-4, respectively), as well as those of the related alkaloids BE-18591 (5) and 6, have been prepared by treatment of bipyrrole aldehyde 16 with the relevant amine in the presence of acetic acid. The 5'-bromo-analogue, 30, of compound 16 has also been prepared and used to obtain the acetate salts of tambjamines G, H, I, and J (8-11 respectively).
Pinkerton
David M
DM
Research School of Chemistry, Institute of Advanced Studies, The Australian National University, Canberra, ACT 0200, Australia.
Banwell
Martin G
MG
Willis
Anthony C
AC
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D018360:Crystallography, X-Ray; D008958:Models, Molecular; D015394:Molecular Structure; D031161:Pseudoalteromonas / Q000737:chemistry*; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000470:Alkaloids; D011758:Pyrroles; C085612:BE 18591