Total synthesis of the cytotoxic anhydrophytosphingosine pachastrissamine (jaspine B).

A short, 8-step synthesis of the marine natural product pachastrissamine has been developed that relies on a diastereoselective aldol reaction between a suitably protected hydantoin and an optically enriched α-chloroaldehyde. This synthetic route provides new opportunities for exploring structure activity relationships within this family of natural products.

A short, organocatalytic formal synthesis of (-)-swainsonine and related alkaloids.

A short synthesis of hydroxyalkyl dihydropyrroles has been developed that involves the coupling of propargylamines with α-chloroaldehydes, followed by Lindlar reduction and a one-pot epoxide formation/opening sequence. The application of this process to the synthesis of unnatural iminosugars and a formal synthesis of (-)-swainsonine is described.