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A Revised Modular Approach to (–)‐ trans ‐Δ 8 ‐THC and Derivatives Through Late‐Stage Suzuki–Miyaura Cross‐Coupling Reactions
Author(s) -
Bloemendal Victor R. L. J.,
Sondag Daan,
Elferink Hidde,
Boltje Thomas J.,
van Hest Jan. C. M.,
Rutjes Floris P. J. T.
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201900059
Subject(s) - chemistry , modular design , coupling (piping) , combinatorial chemistry , coupling reaction , hydride , suzuki reaction , stereochemistry , computational chemistry , medicinal chemistry , organic chemistry , catalysis , palladium , programming language , computer science , mechanical engineering , hydrogen , engineering
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.