A Revised Modular Approach to (–)‐trans‐Δ8‐THC and Derivatives Through Late‐Stage Suzuki–Miyaura Cross‐Coupling Reactions. Issue 12 (18th March 2019)

• Record Type: Journal Article
• Authors: Bloemendal, Victor R. L. J.; Sondag, Daan; Elferink, Hidde; Boltje, Thomas J.; van Hest, Jan. C. M.; Rutjes, Floris P. J. T.
• Is Part Of: European journal of organic chemistry. Issue 12(2019)
• Page Start: 2289
• Page End: 2296
• Publication Date: 2019-03-18
• Subjects: Tetrahydrocannabinol -- Suzuki–Miyaura coupling -- Cannabis derivatives -- Cascade reactions -- Heterocycles; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201900059
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : 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. Abstract : A revised modular approach to various synthetic (–)‐ trans ‐Δ 8 ‐THC derivatives is disclosed. Ten derivatives were sythesized using both sp 2 ‐ and sp 3 ‐hybridized fragment couplings.