Literature DB >> 23346909

Enantioselective total synthesis of (-)-Δ8-THC and (-)-Δ9-THC via catalytic asymmetric hydrogenation and S(N)Ar cyclization.

Li-Jie Cheng1, Jian-Hua Xie, Yong Chen, Li-Xin Wang, Qi-Lin Zhou.   

Abstract

The highly efficient asymmetric total syntheses of (-)-Δ(8)-tetrahydrocannabinol ((-)-Δ(8)-THC) (13 steps, 35%) and (-)-Δ(9)-tetrahydrocannabinol ((-)-Δ(9)-THC) (14 steps, 30%) have been developed by using ruthenium-catalyzed asymmetric hydrogenation of racemic α-aryl cyclic ketones via dynamic kinetic resolution and intramolecular S(N)Ar cyclization.

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Year:  2013        PMID： 23346909     DOI： 10.1021/ol303351y

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  6 in total

1.  Advances in Stereoconvergent Catalysis from 2005 to 2015: Transition-Metal-Mediated Stereoablative Reactions, Dynamic Kinetic Resolutions, and Dynamic Kinetic Asymmetric Transformations.

Authors:  Vikram Bhat; Eric R Welin; Xuelei Guo; Brian M Stoltz
Journal:  Chem Rev       Date:  2017-02-06       Impact factor: 60.622

2.  The Diels-Alder Approach towards Cannabinoid Derivatives and Formal Synthesis of Tetrahydrocannabinol (THC).

Authors:  Thomas Hurrle; Franziska Gläser; Manuel C Bröhmer; Martin Nieger; Stefan Bräse
Journal:  ChemistryOpen       Date:  2021-05       Impact factor: 2.630

3.  Divergent enantioselective synthesis of hapalindole-type alkaloids using catalytic asymmetric hydrogenation of a ketone to construct the chiral core structure.

Authors:  Yang Liu; Li-Jie Cheng; Hai-Tao Yue; Wen Che; Jian-Hua Xie; Qi-Lin Zhou
Journal:  Chem Sci       Date:  2016-04-12       Impact factor: 9.825

4.  Synthesis of [13C4]-labeled ∆9-tetrahydrocannabinol and 11-nor-9-carboxy-∆9-tetrahydrocannabinol as internal standards for reducing ion suppressing/alteration effects in LC/MS-MS quantification.

Authors:  Morten Karlsen; Huiling Liu; Jon Eigill Johansen; Bård Helge Hoff
Journal:  Molecules       Date:  2014-09-01       Impact factor: 4.411

5.  Synthesis of Cannabinoids: "In Water" and "On Water" Approaches: Influence of SDS Micelles.

Authors:  José F Quílez Del Moral; Cristina Ruiz Martínez; Helena Pérez Del Pulgar; Juan Eduardo Martín González; Ignacio Fernández; José Luis López-Pérez; Alejandro Fernández-Arteaga; Alejandro F Barrero
Journal:  J Org Chem       Date:  2021-02-03       Impact factor: 4.198

6.  Synthesis of (-)-Cannabimovone and Structural Reassignment of Anhydrocannabimovone through Gold(I)-Catalyzed Cycloisomerization.

Authors:  Javier Carreras; Mariia S Kirillova; Antonio M Echavarren
Journal:  Angew Chem Int Ed Engl       Date:  2016-04-27       Impact factor: 15.336
  6 in total

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