A Catalytic, Oxidative Synthesis of Olivetol, Methyl Olivetolate and Orthogonally Protected Methyl Ether Derivatives

被引:8
作者
Hurem, David [1 ]
Macphail, Benjamin J. [2 ]
Carlini, Rina [2 ]
Lewis, Jason [2 ]
McNulty, James [1 ]
机构
[1] McMaster Univ, Dept Chem & Chem Biol, 1280 Main St West, Hamilton, ON L8S 4M1, Canada
[2] Rapid Dose Therapeut, 1121 Walkers Line,Suite 3, Burlington, ON L7N 2G4, Canada
关键词
olivetol; olivetolic acid; aromatization; catalysis; oxidation; polyketide; meroterpenoid; PRACTICAL SYNTHESIS; MEDICAL MARIJUANA; CANNABIDIOL; ACID; PHENOLS;
D O I
10.1055/a-1440-9732
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Olivetol, methyl olivetolate and a series of orthogonally protected methyl ether derivatives were synthesized from commonly available precursors using an atom-economical, catalytic oxidative aromatization process.
引用
收藏
页码:86 / 90
页数:5
相关论文
共 41 条
[1]   Pharmacokinetics of Phytocannabinoid Acids and Anticonvulsant Effect of Cannabidiolic Acid in a Mouse Model of Dravet Syndrome [J].
Anderson, Lyndsey L. ;
Low, Ivan K. ;
Banister, Samuel D. ;
McGregor, Iain S. ;
Arnold, Jonathon C. .
JOURNAL OF NATURAL PRODUCTS, 2019, 82 (11) :3047-3055
[2]   A NEW SYNTHESIS OF OLIVETOL [J].
ANKER, RM ;
COOK, AH .
JOURNAL OF THE CHEMICAL SOCIETY, 1945, (MAY) :311-313
[3]   BORON-TRIFLUORIDE ETHERATE ON ALIMINA - A MODIFIED LEWIS ACID REAGENT - AN IMPROVED SYNTHESIS OF CANNABIDIOL [J].
BAEK, SH ;
SREBNIK, M ;
MECHOULAM, R .
TETRAHEDRON LETTERS, 1985, 26 (08) :1083-1086
[4]   Dark Classics in Chemical Neuroscience: Δ9-Tetrahydrocannabinol [J].
Banister, Samuel D. ;
Arnold, Jonathon C. ;
Connor, Mark ;
Glass, Michelle ;
McGregor, Iain S. .
ACS CHEMICAL NEUROSCIENCE, 2019, 10 (05) :2160-2175
[5]   Studies on the resorcylates: biomimetic total syntheses of (+)-montagnetol and (+)-erythrin [J].
Basset, Jean-Francois ;
Leslie, Colin ;
Hamprecht, Dieter ;
White, Andrew J. P. ;
Barrett, Anthony G. M. .
TETRAHEDRON LETTERS, 2010, 51 (05) :783-785
[6]   Blurred Boundaries: The Therapeutics and Politics of Medical Marijuana [J].
Bostwick, J. Michael .
MAYO CLINIC PROCEEDINGS, 2012, 87 (02) :172-186
[7]  
Carberry JJ., 2017, International PatentApplication, Patent No. [2017/091755 A1, 2017091755]
[8]   In vitro and in vivo pharmacology of synthetic olivetol- or resorcinol-derived cannabinoid receptor ligands [J].
Cascio, M. G. ;
Bisogno, T. ;
Palazzo, E. ;
Thomas, A. ;
van der Stelt, M. ;
Brizzi, A. ;
De Novellis, V. ;
Marabese, I. ;
Ross, R. ;
van de Doelen, T. ;
Brizzi, V. ;
Pertwee, R. ;
Maione, S. ;
Di Marzo, V. .
BRITISH JOURNAL OF PHARMACOLOGY, 2006, 149 (04) :431-440
[9]   A BIOMIMETIC SYNTHESIS OF DELTA-1-TETRAHYDROCANNABINOL [J].
CHAN, TH ;
CHALY, T .
TETRAHEDRON LETTERS, 1982, 23 (29) :2935-2938
[10]   A novel phytocannabinoid isolated from Cannabis sativa L. with an in vivo cannabimimetic activity higher than Δ9-tetrahydrocannabinol:Δ9-Tetrahydrocannabiphorol [J].
Citti, Cinzia ;
Linciano, Pasquale ;
Russo, Fabiana ;
Luongo, Livio ;
Iannotta, Monica ;
Maione, Sabatino ;
Lagana, Aldo ;
Capriotti, Anna Laura ;
Forni, Flavio ;
Vandelli, Maria Angela ;
Gigli, Giuseppe ;
Cannazza, Giuseppe .
SCIENTIFIC REPORTS, 2019, 9 (1)