Literature DB >> 17266321

Synthesis of (-)-Delta9-trans-tetrahydrocannabinol: stereocontrol via Mo-catalyzed asymmetric allylic alkylation reaction.

Barry M Trost1, Kalindi Dogra.   

Abstract

[reaction: see text] Delta9-THC is synthesized in enantiomericaly pure form, where all of the stereochemistry is derived from the molybdenum-catalyzed asymmetric alkylation reaction of the extremely sterically congested bis-ortho-substituted cinnamyl carbonate in high regio- and enantioselectivity.

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Year:  2007        PMID： 17266321      PMCID： PMC2597621          DOI： 10.1021/ol063022k

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


  8 in total

1.  Synthesis of functionalized cannabinoids.

Authors:  P E Harrington; I A Stergiades; J Erickson; A Makriyannis; M A Tius
Journal:  J Org Chem       Date:  2000-10-06       Impact factor: 4.354

2.  Synthesis of tetrahydrocannabinols based on an indirect 1,4-addition strategy.

Authors:  Anthony D William; Yuichi Kobayashi
Journal:  J Org Chem       Date:  2002-12-13       Impact factor: 4.354

3.  Novel cannabinol probes for CB1 and CB2 cannabinoid receptors.

Authors:  A Mahadevan; C Siegel; B R Martin; M E Abood; I Beletskaya; R K Razdan
Journal:  J Med Chem       Date:  2000-10-05       Impact factor: 7.446

4.  A TOTAL SYNTHESIS OF DL-DELTA-1-TETRAHYDROCANNABINOL, THE ACTIVE CONSTITUENT OF HASHISH.

Authors:  R MECHOULAM; Y GAONI
Journal:  J Am Chem Soc       Date:  1965-07-20       Impact factor: 15.419

5.  Synthesis and activity of a new generation of ruthenium-based olefin metathesis catalysts coordinated with 1,3-dimesityl-4,5-dihydroimidazol-2-ylidene ligands.

Authors:  M Scholl; S Ding; C W Lee; R H Grubbs
Journal:  Org Lett       Date:  1999-09-23       Impact factor: 6.005

6.  Syntheses of 1 -tetrahydrocannabinol and related cannabinoids.

Authors:  R Mechoulam; P Braun; Y Gaoni
Journal:  J Am Chem Soc       Date:  1972-08-23       Impact factor: 15.419

7.  Classical/nonclassical hybrid cannabinoids: southern aliphatic chain-functionalized C-6beta methyl, ethyl, and propyl analogues.

Authors:  D J Drake; R S Jensen; J Busch-Petersen; J K Kawakami; M Concepcion Fernandez-Garcia; P Fan; A Makriyannis; M A Tius
Journal:  J Med Chem       Date:  1998-09-10       Impact factor: 7.446

8.  A stereospecific synthesis of (-)-delta 1- and (-)-delta 1(6)-tetrahydrocannabinols.

Authors:  R Mechoulam; P Braun; Y Gaoni
Journal:  J Am Chem Soc       Date:  1967-08-16       Impact factor: 15.419
  8 in total
  7 in total

1.  Pd and Mo Catalyzed Asymmetric Allylic Alkylation.

Authors:  Barry M Trost
Journal:  Org Process Res Dev       Date:  2012-01-13       Impact factor: 3.317

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.  Highly enantioselective access to cannabinoid-type tricyles by organocatalytic Diels-Alder reactions.

Authors:  Stefan Bräse; Nicole Volz; Franziska Gläser; Martin Nieger
Journal:  Beilstein J Org Chem       Date:  2012-08-28       Impact factor: 2.883

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

Review 6.  Discovery and resupply of pharmacologically active plant-derived natural products: A review.

Authors:  Atanas G Atanasov; Birgit Waltenberger; Eva-Maria Pferschy-Wenzig; Thomas Linder; Christoph Wawrosch; Pavel Uhrin; Veronika Temml; Limei Wang; Stefan Schwaiger; Elke H Heiss; Judith M Rollinger; Daniela Schuster; Johannes M Breuss; Valery Bochkov; Marko D Mihovilovic; Brigitte Kopp; Rudolf Bauer; Verena M Dirsch; Hermann Stuppner
Journal:  Biotechnol Adv       Date:  2015-08-15       Impact factor: 14.227

7.  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
  7 in total

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