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- Title
Short and Divergent Total Synthesis of (+)-Machaeriol B, (+)-Machaeriol D, (+)-Δ<sup>8</sup>-THC, and Analogues.
- Authors
Klotter, Felix; Studer, Armido
- Abstract
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.
- Subjects
CANNABINOIDS; MACHAERITES; STEREOSELECTIVE reactions; PALLADIUM catalysts; TETRAHYDROCANNABINOL; DECARBOXYLATION; ARYLATION
- Publication
Angewandte Chemie International Edition, 2015, Vol 54, Issue 29, p8547
- ISSN
1433-7851
- Publication type
Article
- DOI
10.1002/anie.201502595