Premium
Synthesis of olivetol‐4,6− 14 C 2 , and its conversion to (–)–δ 9 ‐6a, 10a‐ trans ‐tetrahydrocannabinol‐2,4− 14 C 2 via (–)–Δ 8 ‐6a, 10a‐ trans ‐tetrahydrocannabinol‐2,4− 14 C 2
Author(s) -
Liebman A. A.,
Malarek D. H.,
Dorsky A. M.,
Kaegi H. H.
Publication year - 1971
Publication title -
journal of labelled compounds
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0022-2135
DOI - 10.1002/jlcr.2590070307
Subject(s) - diethyl malonate , chemistry , malonate , yield (engineering) , hydrolysis , medicinal chemistry , chromatography , nuclear chemistry , organic chemistry , catalysis , thermodynamics , physics
Olivetol‐4,6− 14 C 2 (III) was prepared by condensing diethyl‐malonate‐2− 14 C with 3‐nonen‐2‐one followed by hydrolysis, decar‐boxylation and oxidation. Reaction with (+)‐trans‐p‐menthadien‐2,8‐ol‐l provided (–) — Δ 8 6a, 10a‐trans‐tetrahydrocannabinol‐2,4− 14 C 2 (IV) which was isomerized to (–) — Δ 9 ‐6a, 10a‐trans‐tetrahydrocannabinol‐2,4− 14 C 2 (V). On a scale of 3–5 mmole, malonate‐2− 14 C yields 45–50% of chromatographically pure olivetol‐4,6− 14 C 2 , which on a 2 mmole scale, gave a 56% radiochemical yield of purified tetrahydrocannabinols. Both the (–) — Δ 8 ‐THC‐2,4− 14 C 2 and (–) — Δ 9 ‐THC‐2,4− 14 C 2 had greater [α] D than previously reported.