Synthesis of squalamine utilizing a readily accessible spermidine equivalent

Squalamine was efficiently prepared in five steps utilizing a latent spermidine reagent. This reagent was shown to be most appropriate, as it is stable to reductive amination conditions. It is converted to spermidine under weakly acidic conditions. The soybean-based sterol, stigmasterol, which is used as the starting material to prepare the key intermediate, is both inexpensive and readily available. This stereoselective synthesis of squalamine from steroid has provided supplies for phase I clinical trials.