Asymmetric Synthesis of (-)-Cannabidiol (CBD), (-)-Δ9-Tetrahydrocannabinol (Δ9-THC) and Their cis Analogs Using an Enantioselective Organocatalyzed Diels-Alder Reaction

被引：2

作者：

Pauvert, Yann ^{[1
]}

Charette, Andre B. ^{[1
]}

机构：

[1] Univ Montreal, Ctr Continuous Flow Synth, Dept Chim, FRQNT Ctr Green Chem & Catalysis, Montreal, PQ H2V 0B3, Canada

来源：

ORGANIC LETTERS | 2024年 / 26卷 / 29期

基金：

加拿大自然科学与工程研究理事会; 加拿大创新基金会;

关键词：

MICHAEL REACTION; CANNABINOIDS; ALDEHYDES;

D O I：

10.1021/acs.orglett.4c01622

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Herein we describe an asymmetric synthesis of the pharmacologically relevant natural (-)-trans-CBD and psychoactive (-)-trans-Delta(9)-THC, as well as their synthetic cis diastereomers. The key step is an enantioselective Diels-Alder reaction catalyzed by a prolinol-based catalyst, which provides the cyclohexene carbaldehyde intermediate in good yield and high enantiomeric excess. Optimization of the substituted resorcinol protecting groups to avoid harsh and low-yield deprotection of the acid sensitive resorcinol moiety is also described.

引用

页码：6081 / 6085

页数：5

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