During the large-scale isolation of the batzelladines A and B, which a
re inhibitors of gp120-CD4 binding, we isolated 19 minor guanidine alk
aloids. Three new tricyclic guanidine alkaloids isolated from this gro
up were named 8a,8b-dehydroptilocaulin (2), 8a,8b-dehydro-8-hydroxypti
locaulin (3), and 1,8a;8b,3a-didehydro-8-hydroxyptilocaulin (5). The r
ecently described mirabilin B (4) was also isolated. The structures an
d relative stereochemistry of these compounds were determined by spect
ral analysis and by comparison with spectral data of ptilocaulin (1).