Hashish : Synthesis of (+)-Δ-tetrahydrocannabinol

Alkylation of olivetol with p-menth-4-en-3,8-diol (3) afforded Δ⁴-tetrahydrocannabinol, an unknown isomer of the hashish active constituent Δ¹-THC, together with the “abnormal” isomer. The attack of olivetol onto the positions 3 and 5 and resp. 3 and 8 of (3) yielded derivatives of 2,6-methano-2H,1-benzoxocin-7-ol and new 2,3,4,4a-tetrahydroxanthenes.