Total Synthesis of (‐)‐Cannabidiol‐C4

Cannabidiol-C-4 1 (CBD-C-4, cannabidibutol) is a natural product that is present in the extracts of Cannabis. Its isolation has not been reported to date. The aim of the proposed synthesis is to secure the availability of the pure compound, its spectroscopic characterization, and to confirm its presence in low amounts in the extracts. The enantioselective total synthesis is based on a) the use 3,5-dimetoxybenzaldehyde as starting material, b) Corey-Bakshi-Shibata reduction, c) Claisen-Ireland rearrangement, d) ring-closing metathesis, and e) completely not-trivial demethylation induced by sodium ethanethiolate.