ArticleChemistry (Weinheim an der Bergstrasse, Germany)2021
A Protecting-Group-Free Synthesis of (-)-Salvinorin A.
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 4 papers.
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4 citing papers in PubMed.
- A Route to Potent, Selective, and Biased Salvinorin Chemical Space.ACS central science · 2023Article
- Sharpless Asymmetric Dihydroxylation: An Impressive Gadget for the Synthesis of Natural Products: A Review.Molecules (Basel, Switzerland) · 2023Review
- Formal Total Synthesis of Salvinorin A.ChemistryOpen · 2022Article
- A Protecting-Group-Free Synthesis of (-)-Salvinorin A.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Article
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3 authors.
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Abstract
A concise enantioselective total synthesis of the neoclerodane diterpene (-)-salvinorin A is reported. The stereogenic center at C-12 was installed by catalytic asymmetric propargylation with excellent enantioselectivity, and the remaining six stereogenic centers were set up highly diastereoselectively under substrate control. As for our previous synthesis of racemic salvinorin A, two intramolecular Diels-Alder reactions were applied to generate the tricyclic core. A chemoselective Mitsunobu inversion of a syn 1,2-diol allowed for further streamlining of the original reaction sequence by two steps. Overall, (-)-salvinorin A was synthesized in only 16 steps starting from 3-furaldehyde with 1.4 % total yield. Furthermore, an alternative intramolecular Diels-Alder strategy employing a 2-bromo-1,3-diene moiety was investigated.
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