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Synthesis of [5,6‐ 13 C 2 , 1‐ 14 C]olivetolic acid, methyl [1′‐ 13 C]olivetolate and [5,6‐ 13 C 2 , 1‐ 14 C]cannabigerolic acid
Author(s) -
Porwoll Joseph P.,
Leete Edward
Publication year - 1985
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580220307
Subject(s) - chemistry , acetylide , bromide , lithium (medication) , hydrolysis , carbon 13 nmr , malonate , acid hydrolysis , stereochemistry , medicinal chemistry , organic chemistry , medicine , endocrinology
Potential advanced intermediates in the biosynthesis of Δ 9 ‐tetrahydrocannabinol have been synthesized labeled with two contiguous 13 C atoms and 14 C. Methyl [5,6‐ 13 C 2 , 1‐ 14 C]olivetolate was prepared from lithium [ 13 C 2 ]acetylide and dimethyl [2‐ 14 C]malonate. Reaction with geranyl bromide afforded methyl [5,6‐ 13 C 2 , 1‐ 14 C]cannabigerolate, and hydrolysis of these methyl esters with lithium propyl mercaptide yielded the corresponding labeled acids. The 13 C‐ 13 C couplings observable in the 13 C NMR spectra of these 13 C‐enriched compounds and their synthetic precursors are recorded. Methyl [1′‐ 14 C]olivetolate was prepared from 13 CO 2 to confirm assignments of the 13 C chemical shifts in the pentyl side chain of these compounds.