Sauerstoffanaloge Δ⁸- und Δ⁹-Tetrahydrocannabinole.

Abstract

The phloroglucine derivatives (2 a–h) react with (+)-trans-p-menthadien-(2,8)-ol-(1) to give the oxygen analogous of (—)-Δ8-tetrahydrocannabinole such as 3 a–h. Some of these derivatives were converted by HCl-addition/elimination into the isomeric Δ9-compounds. The proposed structures of the derivatives are supported by spectroscopic data (1H NMR, IR and MS).

Synthesis of Para (−)-Δ8-THC Triflate as a Building Block for the Preparation of THC Derivatives Bearing Different Side Chains

“…Unfortunately, in our initial paper the structure, based on a literature report was not correctly assigned. Such ortho THC regioisomers have occasionally been mentioned as side products in reactions of resorcinols with terpene derivatives, especially when rather small meta substituents are attached to the resorcinol component, and the corresponding regioisomeric products were categorized as “abnormal” THCs. − For example, Antoniotti et al used this “reversed” selectivity to prepare several ortho -THCs in flow . To circumvent this regioselectivity problem and to access a general THC building block for late-stage diversification of the para position, we envisioned using the symmetric phloroglucinol as the resorcinol reaction component in such a cascade.…”

A Revised Modular Approach to (–)‐trans‐Δ8‐THC and Derivatives Through Late‐Stage Suzuki–Miyaura Cross‐Coupling Reactions

“…Inversely, existing syntheses of bromo-substituted THCs [11,15] by alkylating 5-bromoresorcinol 5 with terpenoid systems such as verbenol (2) and para-mentha-2,8-dienol, inspired us to incorporate different synthetic handles in the Δ 8 -THC derivatives. Hence, halide-substituted THC scaffolds were prepared through TfOH-catalyzed condensation of resorcinol 5 (Scheme 3).…”

Synthetic pathways to tetrahydrocannabinol (THC): an overview

“…Without the use of any chiral catalyst present, an unseparable complex mixture of all possible CBD analogues was obtained. 53,54 The first asymmetric synthesis of the unnatural isomer (+)-trans-Δ 9 -THC (59) using a Diels-Alder reaction was reported by Evans, Shaughnessy and Barnes (Scheme 13). 55 Key-step was the synthesis of the acetylated cycloadduct 57 on 50 mmol scale.…”