112639-16-4Relevant articles and documents
Short and Divergent Total Synthesis of (+)-Machaeriol B, (+)-Machaeriol D, (+)-Δ8-THC, and Analogues
Klotter, Felix,Studer, Armido
, p. 8547 - 8550 (2015)
Short and highly efficient stereoselective syntheses provide machaeriols and cannabinoids in a divergent approach starting from a common precursor, commercially available (S)-perillic acid. Key features of the novel strategy are a stereospecific palladium-catalyzed decarboxylative arylation and a one-pot sequence comprising a stereoselective hydroboration followed by oxidation or reduction of the corresponding intermediary boranes. The divergent approach is convincingly demonstrated by the five-step syntheses of (+)-machaeriol B, (+)-machaeriol D, and related analogues, and the four-step synthesis of (+)-Δ8-THC and an analogue.
Halogenation of Phenols and Phenyl Ethers with Potassium Halides in the Presence of 18-Crown-6 on Oxidation with m-Chloroperbenzoic Acid
Srebnik, Morris,Mechoulam, Raphael,Yona, Irene
, p. 1423 - 1428 (2007/10/02)
Several types of phenyl ethers have been monobrominated in the ring in good yields with potassium bromide in the presence of 18-crown-6 on oxidation with m-chloroperbenzoic acid.Monoiodination takes place with both phenyl ethers and free phenols when potassium iodide is employed.