Stereocontrolled Intramolecular Diels‐Alder Reaction of Heterodienes; Studies on the Synthesis of Cannabinoids

Abstract

The skeleton (4) of tetrahydrocannabinol having translinked rings A and B can be obtained optically pure from the diketone (1) and (R)-citronellal (2). The key step is intramolecular Diels-Alder reaction (up to 20°C!) of the heterodiene intermediate (3).—Derivatives of (4) are of interest, e.g., in the treatment of glaucoma.