Drugs derived from Cannabinoids. Part 8. The Synthesis of Side-chain Analogues of Δ6a,10a-Tetrahydrocannabinol

DOI: 10.1039/P19810002825

Source and publish data:

Journal of the Chemical Society. Perkin transactions I p. 2825 - 2829 (1981)

Update date:2022-08-03

Topics: Propargylation Phase-transfer catalysis

Authors:

Meltzer, Peter C.

Dalzell, Haldean C.

Razdan, Raj K.

Read Full Text PDF DownLoad Join now for total 90,000,000 free articles

Article abstract of DOI:10.1039/P19810002825

The continuation of studies on the synthesis of side-chain analogues of Δ^6a,10a-tetrahydrocannabinol as potential therapeutic agents has led to the syntheses of a possible metabolite 1-hydroxy-6,6,9-trimethyl-7,8,9,10-tetrahydro-6H-dibenzopyran-3-ylacetic acid (1) and 2-(1-hydroxy-6,6,9-trimethyl-7,8,9,10-tetrahydro-6H-dibenzopyran-3-yl)pent-4-ynoic acid (17c).The Pechmann condensation of ethyl 4-methyl-2-oxocyclohexane-1-carboxylate with methyl 3,5-dihydroxyphenylacetate (11), followed by Grignard reaction, was utilized to produce the pyran (1).The key step in the synthesis of the propargylacetic acid (17c) was propargylation of the malonate (15) under phase-transfer catalysis.

Full text of DOI:10.1039/P19810002825

View Article Online / Journal Homepage / Table of Contents for this issue

View Article Online

Products guided by the article

Product name:ethyl 2-(3,5-bisbenzyloxyphenyl)-2-methoxycarbonylacetate

Cas No:80457-65-4

R&D Labs maybe for 80457-65-4

Tianjin Hedong Red Cliff Chemical Reagent Factory

Contact:+86-022-84780548

Address:Li Ming Zhuang Gong Ye Yuan,Dongli District,Tianjin,China
VanderArk International Limited

Contact:86-10-82437576

Address:Qing He
Liao Cheng All Win Chemicals Co.,LTD

Contact:86+0635-2991582

Address:Room 402,Unit 1,No.27 building.Zhong tong shi dai haoyuan,liaocheng city,Shan dong Province.China
Nanjing yieldpharma co.ltd

Contact:13813902930 025-52714267

Address:20 Fengji Road, Yuhua Economic Development Zone, Nanjing, Jiangsu, P. R. China
Shanghai doly chemical Co.,Ltd

Contact:+86-21-34716221

Address:No.328,WuHe Roard,MinHang,ShangHai China

Relevant to this article

Synthesis of new tridentate chiral aminoalcohols by a multicomponent reaction and their evaluation as ligands for catalytic asymmetric Strecker reaction

Doi:10.1016/j.tet.2007.06.047
(2007)
Urea host monomers for stoichiometric molecular imprinting of oxyanions

Doi:10.1021/jo048470p
(2005)
Aluminium(III) Chloride-Catalyzed Three-Component Condensation of Aromatic Aldehydes, Nitroalkanes and Sodium Azide for the Synthesis of 4-Aryl-NH-1,2,3-triazoles

Doi:10.1002/adsc.201600098
(2016)
PHOTOFRAGMENTATION OF OXAZOLIDINES. A NEW METHOD FOR THE GENERATION OF AZIRIDINES

Doi:10.1246/cl.1981.1585
(1981)
THE SYNTHESIS OF VAFZELIN AND SYNCARPIN, CONSTITUTENTS OF UVARIA AFZELII

Doi:10.1016/S0040-4039(01)81906-7
(1981)
THE PREPARATION OF BILE ACID AMIDES AND OXAZOLINES

Doi:10.1016/0039-128X(81)90068-4
(1981)

Article Doi