Abstract
Antillidine (9), a natural product isolated from Solanum antillarum by Coll et al. in 1992, was synthesized successfully in two steps in 70% overall yields from nature diosgenin. Similar to antillidine (9) is that squalamine also has an amino group attached to the steroid nucleus. On the other hand, squalamine is an aminosterol, which was isolated from tissues of dogfish shark Squalus acanthias by Moore et al. in 1993. Squalamine has gained great attention from scientists because of its antiangiogenic and antitumor activities. The compound possesses an amino side chain at the C-3 position. We planned to develop a strategy for the synthesis of squalamine derivatives by linking antillidine (9) with different amino side chains; meanwhile the products possessed a spiro structure at the C-16 and the C-17 positions of steroid. Six different lengths of side chains containing two nitrogen atoms were also synthesized in good yields (55–65%).