33029-18-4Relevant articles and documents
Short and Divergent Total Synthesis of (+)-Machaeriol B, (+)-Machaeriol D, (+)-Δ8-THC, and Analogues
Klotter, Felix,Studer, Armido
, p. 8547 - 8550 (2015/11/27)
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.
High-pressure diels-alder cycloadditions between benzylideneacetones and 1,3-Butadienes: Application to the synthesis of (R,R)-(-)- and (S,S)-(+)-Δ8-tetrahydrocannabinol
Ballerini, Eleonora,Minuti, Lucio,Piermatti, Oriana
supporting information; experimental part, p. 4251 - 4260 (2010/09/05)
High-pressure Diels-Alder reactions of various alkoxy/alkyl-substituted benzylideneacetones with methyl-1,3-butadienes are reported. Activation by high pressure (8-11 kbar) in combination with the mild Lewis acid HfCl 42THF allows these reactions to efficiently and regioselectively produce a series of ortho-substituted cyclohexenyl-benzene cycloadducts, that are useful precursors for the expeditious construction of the privileged 6,6-dimethyltetrahydro-6H-benzo[c]chromene skeleton. Application to the synthesis of Δ8-trans-THC in both enantiomeric pure forms is based on the successful resolution of selected cycloadduct by the SAMP-hydrazone method.