Synthesis of the fatty acid of pramanicin

The natural product tetradec-2-enoic acid-4,5-epoxide (2), which is also a component of the antibiotic pramanicin (1), was prepared in racemic form by a glycoluril-template directed approach. Two sequential additions of acetate units to decanoic acid are effected by intramolecular condensations on the template, mimicking the proposed biosynthetic pathway to 1. Cleavage of the grown trans,trans-tetradeca-2,4-dienoyl chain from the template and epoxidation yields 2. The reaction sequence illustrates the applicability of this biomimetic approach to total synthesis of natural products.