Total Synthesis of (-)-Salvinorin A.
Chemistry (Weinheim an der Bergstrasse, Germany) December 12, 2016 Nathan J Line, Aaron C Burns, Sean C Butler et al. 41 citations
Salvinorin A (1) is natural hallucinogen that binds the human κ-opioid receptor. A total synthesis has been developed that parlays the stereochemistry of l-(+)-tartaric acid into that of (-)-1 via an unprecedented allylic dithiane intramolecular Diels-Alder reaction to obtain the trans-decalin scaffold. Tsuji allylation set the C9 quaternary center and a late-stage stereoselective chiral...