ArticleChemistryOpen2022
Formal Total Synthesis of Salvinorin A.
Article in ChemistryOpen, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 3 papers.
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Who cites it
3 citing papers in PubMed.
- Comparative genome analysis provides a foundation for defining salvinorin A biosynthesis in Salvia divinorum.Nature communications · 2026Article
- A Route to Potent, Selective, and Biased Salvinorin Chemical Space.ACS central science · 2023Article
- Formal Total Synthesis of Salvinorin A.ChemistryOpen · 2022Article
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Authors and funding
2 authors.
Funding
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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.
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