A Revised Modular Approach to (–)‐trans‐Δ(8)‐THC and Derivatives Through Late‐Stage Suzuki–Miyaura Cross‐Coupling Reactions

A revised modular approach to various synthetic (–)‐trans‐Δ(8)‐THC derivatives through late‐stage Suzuki–Miyaura cross‐coupling reactions is disclosed. Ten derivatives were synthesized allowing both sp(2)‐ and sp(3)‐hybridized cross‐coupling partners with minimal β‐hydride elimination. Importantly,...

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Autores principales: Bloemendal, Victor R. L. J., Sondag, Daan, Elferink, Hidde, Boltje, Thomas J., van Hest, Jan. C. M., Rutjes, Floris P. J. T.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2019
Materias:
Full Papers
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6686972/
https://www.ncbi.nlm.nih.gov/pubmed/31423106
http://dx.doi.org/10.1002/ejoc.201900059
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author Bloemendal, Victor R. L. J.
Sondag, Daan
Elferink, Hidde
Boltje, Thomas J.
van Hest, Jan. C. M.
Rutjes, Floris P. J. T.
author_facet Bloemendal, Victor R. L. J.
Sondag, Daan
Elferink, Hidde
Boltje, Thomas J.
van Hest, Jan. C. M.
Rutjes, Floris P. J. T.
author_sort Bloemendal, Victor R. L. J.
collection PubMed
description A revised modular approach to various synthetic (–)‐trans‐Δ(8)‐THC derivatives through late‐stage Suzuki–Miyaura cross‐coupling reactions is disclosed. Ten derivatives were synthesized allowing both sp(2)‐ and sp(3)‐hybridized cross‐coupling partners with minimal β‐hydride elimination. Importantly, we demonstrate that a para‐bromo‐substituted THC scaffold for Suzuki–Miyaura cross‐coupling reactions has been initially reported incorrectly in recent literature.
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spelling pubmed-66869722019-08-14 A Revised Modular Approach to (–)‐trans‐Δ(8)‐THC and Derivatives Through Late‐Stage Suzuki–Miyaura Cross‐Coupling Reactions Bloemendal, Victor R. L. J. Sondag, Daan Elferink, Hidde Boltje, Thomas J. van Hest, Jan. C. M. Rutjes, Floris P. J. T. European J Org Chem Full Papers A revised modular approach to various synthetic (–)‐trans‐Δ(8)‐THC derivatives through late‐stage Suzuki–Miyaura cross‐coupling reactions is disclosed. Ten derivatives were synthesized allowing both sp(2)‐ and sp(3)‐hybridized cross‐coupling partners with minimal β‐hydride elimination. Importantly, we demonstrate that a para‐bromo‐substituted THC scaffold for Suzuki–Miyaura cross‐coupling reactions has been initially reported incorrectly in recent literature. John Wiley and Sons Inc. 2019-03-18 2019-03-31 /pmc/articles/PMC6686972/ /pubmed/31423106 http://dx.doi.org/10.1002/ejoc.201900059 Text en © 2019 The Authors. Published by Wiley‐VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the http://creativecommons.org/licenses/by/4.0/ License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
spellingShingle Full Papers
Bloemendal, Victor R. L. J.
Sondag, Daan
Elferink, Hidde
Boltje, Thomas J.
van Hest, Jan. C. M.
Rutjes, Floris P. J. T.
A Revised Modular Approach to (–)‐trans‐Δ(8)‐THC and Derivatives Through Late‐Stage Suzuki–Miyaura Cross‐Coupling Reactions
title A Revised Modular Approach to (–)‐trans‐Δ(8)‐THC and Derivatives Through Late‐Stage Suzuki–Miyaura Cross‐Coupling Reactions
title_full A Revised Modular Approach to (–)‐trans‐Δ(8)‐THC and Derivatives Through Late‐Stage Suzuki–Miyaura Cross‐Coupling Reactions
title_fullStr A Revised Modular Approach to (–)‐trans‐Δ(8)‐THC and Derivatives Through Late‐Stage Suzuki–Miyaura Cross‐Coupling Reactions
title_full_unstemmed A Revised Modular Approach to (–)‐trans‐Δ(8)‐THC and Derivatives Through Late‐Stage Suzuki–Miyaura Cross‐Coupling Reactions
title_short A Revised Modular Approach to (–)‐trans‐Δ(8)‐THC and Derivatives Through Late‐Stage Suzuki–Miyaura Cross‐Coupling Reactions
title_sort revised modular approach to (–)‐trans‐δ(8)‐thc and derivatives through late‐stage suzuki–miyaura cross‐coupling reactions
topic Full Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6686972/
https://www.ncbi.nlm.nih.gov/pubmed/31423106
http://dx.doi.org/10.1002/ejoc.201900059
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