Total syntheses of tambjamines C, E, F, G, H, I and J, BE-18591, and a related alkaloid from the marine bacterium Pseudoalteromonas tunicata

David M Pinkerton; Martin G Banwell; Anthony C Willis

doi:10.1021/ol7024313

Total syntheses of tambjamines C, E, F, G, H, I and J, BE-18591, and a related alkaloid from the marine bacterium Pseudoalteromonas tunicata

Org Lett. 2007 Nov 22;9(24):5127-30. doi: 10.1021/ol7024313. Epub 2007 Oct 27.

Authors

David M Pinkerton¹, Martin G Banwell, Anthony C Willis

Affiliation

¹ Research School of Chemistry, Institute of Advanced Studies, The Australian National University, Canberra, ACT 0200, Australia.

PMID: 17963401
DOI: 10.1021/ol7024313

Abstract

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).

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkaloids / chemical synthesis*
Alkaloids / chemistry
Crystallography, X-Ray
Models, Molecular
Molecular Structure
Pseudoalteromonas / chemistry*
Pyrroles / chemical synthesis*
Pyrroles / chemistry
Stereoisomerism

Substances

Alkaloids
Pyrroles
BE 18591