Revision of the stereochemistry of batzelladine F. Approaches to the tricyclic hydroxyguanidine moiety of batzelladines G, H, and I.
The polycyclic guanidine alkaloids batzelladines F-I isolated from a Jamaican sponge of the genus Batzella in 1997 are of potential value for the treatment of AIDS because they induce p56lck-CD4 dissociation at micromolar concentrations. Comparison of the spectral data for both the synthetic syn and anti tricyclic left-hand portions of batzelladine F establishes that the natural product has the syn rather than the anti stereochemistry originally assigned. Approaches to the tricyclic hydroxyguanidine moiety of batzelladines G-I are described.
Snider
B B
BB
Department of Chemistry, Brandeis University, Waltham, Massachusetts 02454-9110, USA. snider@brandeis.edu
Busuyek
M V
MV
D000818:Animals; D006575:Heterocyclic Compounds, 3-Ring / Q000737:chemistry*; D008956:Models, Chemical; D011161:Porifera / Q000737:chemistry*; D013237:Stereoisomerism
D006575:Heterocyclic Compounds, 3-Ring