222528-46-3Relevant academic research and scientific papers
Octadehydromichellamine, a structural analog of the anti-HIV michellamines without centrochirality
Bringmann, Gerhard,Wenzel,Kelly, T. Ross,Boyd, Michael R.,Gulakowski, Robert J.,Kaminsky, Ronald
, p. 1731 - 1740 (1999)
The synthesis of octadehydromichellamine (4), as the fully dehydrogenated structural analog of the naturally occurring michellamines (1), is described. This derivative is the first michellamine-type quateraryl without centrochirality and thus constitutes a distinctly simplified structural michellamine analog. Key step of the total synthesis is the twofold coupling of a bis-O-triflate activated central binaphthalene building block 9 with 2 eq. of the isoquinoline boronic acid 8, to give the quateraryl 11, whose deprotection delivers the target molecule 4, in an apparently stereochemically pure form. Octadehydromichellamine (4) shows a good order of anti-HIV activity and, compared with natural michellamines, enhanced antimalarial activity against Plasmodium falciparum.
