Formal Total Synthesis of Salvinorin A
Marc Halang, Martin E. Maier
ChemistryOpen October 26, 2022 DOI: 10.1002/open.202200015 (opens in new tab)
Study at a glance
AI-extracted from the abstract| Characteristics | Peer reviewed |
|---|---|
| Topics | Salvia divinorum |
| Keywords | Cyanohydrin Decalins Johnson-claisen rearrangement Wieland-miescher ketone |
| Key points | The Johnson-Claisen rearrangement of an allyl alcohol derived from a Wieland-Miescher ketone produced two diastereomeric 1,4-unsaturated esters in a ratio of approximately 2.6:1, and the major isomer was converted to a key intermediate of the Hagiwara synthesis of salvinorin A. |
Abstract
Abstract The generation of the quaternary stereocenter at the C9 position of salvinorin A precursors by the Claisen rearrangement was investigated. The required allyl alcohol was prepared from a Wieland‐Miescher ketone using a known γ‐hydroxylation, reduction of the enone double bond, cyanohydrin formation, and elimination, yielding an unsaturated nitrile. A two‐step reduction led to the required allyl alcohol. The subsequent Johnson‐Claisen rearrangement provided a mixture of two diastereomeric 1,4‐unsaturated esters in a ratio of around 2.6 : 1. The major isomer could be converted to a key intermediate of the Hagiwara synthesis of salvinorin A.
Citations in the library
Cited by 6
- Heteroaromatic salvinorin A analogue (P-3 l) elicits antinociceptive and anxiolytic-like effects. Fitoterapia June 1, 2023
- Comparative genome analysis provides a foundation for defining salvinorin A biosynthesis in Salvia divinorum Nature Communications March 23, 2026
- An Overview of Syntheses of Salvinorin A and its Analogues ChemCatChem August 26, 2024
- Formal Synthesis of (±)-Salvinorin A via Gold(I) Catalysis. Chemistry - A European Journal September 1, 2023
- A Route to Potent, Selective, and Biased Salvinorin Chemical Space. ACS Central Science August 23, 2023
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- Total Synthesis of the Neoclerodane Diterpene Salvinorin A via an Intramolecular Diels–Alder Strategy Organic Letters May 22, 2018
- Chemical syntheses of the salvinorin chemotype of KOR agonist. Natural Product Reports November 18, 2020
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