Synthesis of vulpinic acids from dimethyl tartrate

A series of vulpinic acids differing by the aryl or heteroaryl groups placed in the ester α-position were prepared by Suzuki–Miyaura cross-coupling involving a common iodide and the corresponding aryl boronates. The preparation of the iodide precursor from (+)-dimethyl l-tartrate required four steps: the esterification of one hydroxyl group, a Dieckmann cyclization allowing the construction of the tetronic acid moiety, a dehydration leading to the installation of the exocyclic double bond and lastly, an N-iodosuccinimide-mediated iodation of the alkene obtained.

Graphical abstractVulpinic acids were prepared by Suzuki–Miyaura cross-coupling involving a common iodoalkene, obtained in a few steps, including a Dieckmann cyclization, from (+)-dimethyl l-tartrate.Figure optionsDownload full-size imageDownload as PowerPoint slide