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Total Synthesis of (−)‐Salvinorin A |
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| Authors: | Dr Nathan J Line Dr Aaron C Burns Prof?Dr Sean C Butler Jerry Casbohm Prof?Dr Craig J Forsyth |
| Affiliation: | 1. Department of Chemistry and Biochemistry, The Ohio State University, Columbus, OH, USA;2. Dart NeuroScience LLC, San Diego, CA, USA;3. Department of Chemistry and Biochemistry, The University of Texas at Tyler, Tyler, TX, USA;4. (+1)?614‐292‐1685
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| Abstract: | 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 ligand‐assisted addition of a 3‐titanium furan upon a C12 aldehyde/C17 methyl ester established the furanyl lactone moiety. The tartrate diol was finally converted into the C1,C2 keto‐acetate. |
| Keywords: | Diels– Alder reaction natural products neurochemistry synthetic methods xenobiotics |
