Vinamidinium salts and β-chloroenals were utilized for the development of two synthetic routes towards the biologically active marine alkaloid Lamellarin G trimethyl ether. Both routes culminated at a key intermediate previously prepared by Wolfgang Steglich and co-workers in their total synthesis of Lamellarin G trimethyl ether. The route employing vinamidinium salts reached the Steglich synthon in ten steps and is modular in nature, making it amenable for structure activity relationship studies.

Zinc(II) bromide catalyzes the addition of terminal acetylenes to both saturated and unsaturated aldehydes in good to excellent yield at room temperature in the presence of trimethylsilyl trifluoromethanesulfonate (TMSOTf) and Hunig's base (i-Pr2NEt). No reaction is observed under similar conditions in the absence of TMSOTf. Desilylation of the initial product provides access to synthetically useful propargyllic alcohols.