Total Synthesis of (-)-Salvinorin A.
Nathan J Line, Aaron C Burns, Sean C Butler, Jerry Casbohm, Craig J Forsyth
Chemistry (Weinheim an der Bergstrasse, Germany) December 12, 2016 DOI: 10.1002/chem.201604853 via PubMed
Summary
AI-generated from the abstractUnderstanding how natural products like Salvinorin A interact with our neurochemistry is crucial. Researchers successfully developed innovative synthetic methods to create this complex molecule from a simple starting material. A key step involved an unprecedented Diels-Alder reaction, efficiently building its intricate core structure. This breakthrough in organic synthesis provides a new pathway to access this important compound, enabling deeper exploration into how such xenobiotics affect brain receptors.
Study at a glance
| Characteristics | Theoretical or philosophical paper Peer reviewed |
|---|---|
| Topics | Salvia divinorum |
| Keywords | Diels-alder reaction Natural products Neurochemistry Synthetic methods Xenobiotics |
| Citations | 41 |
| Key finding | A total synthesis of salvinorin A has been developed using a series of novel chemical reactions. |
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.