Diastereoselective Pictet-Spengler reactions of L-(Boc)prolinal: A biomimetic synthesis of eudistomins H and I, and woodinine

Article abstract of DOI:10.1016/S0040-4039(00)93484-1

The carbon skeleton present in eudistomins H, I and woodinine may be envisioned to be biosynthetically derived from tryptamine and L-prolinal by a Pictet-Spengler type reaction. The diastereoselectivity (> 5:1) of this reaction, and the elaboration of the Pictet-Spengler products into the title compounds is described. The absolute stereochemistry of (-) woodinine is thereby established.