Preparation of Analogues of Territrem B, a Potent AChE Inhibitor

The synthesis of analogues of the potent acetylcholinesterase inhibitor, Territrem B, was carried out starting from the naturally occurring jujubogenin glycosides. Dihydrojujubogenin-2-en-1-one (1), a dammarane derivative that possesses a skeleton and pharmacophore partially similar to those of Territrem B, was synthesized via three different paths. The derivative 21, which contains two potential pharmacophores, was also synthesized. The anti-AChE activity of the analogues was measured. The aromatic ring moiety seemed to be less important when compared with the 2-en-1-one pharmacophore.