Formal Synthesis of (±)‐Salvinorin A via Gold(I) Catalysis

Tran, Huy; McGee, Philippe; Barriault, Louis

doi:10.1002/chem.202301640

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Formation Of Carbocycles1

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2024

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Cited by 2 publications

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“…67 Most recently, Barriault and co-workers reported a formal synthesis of salvinorin A ( 68 ) by utilizing two robust gold( i )-catalyzed cyclizations (Scheme 10). 68 The cyclization of silyl ether 64 was catalyzed by 10 mol% [JohnPhosAuNCMe]SbF 6 in a mixed solvent (DCM/acetone = 20 : 1) at room temperature, affording decalin intermediate 65 in 76% isolated yield with gratifying regioselectivity. Subsequently, bromide 66 underwent a radical cyclization initiated by 10 mol% [Au 2 (dppm) 2 ]Cl 2 in the presence of DIPEA under UV light.…”

Section: Formation Of Carbocyclesmentioning

confidence: 99%

Gold-catalyzed cyclization and cycloaddition in natural product synthesis

Lin,

Liu,

Luo

2024

Nat. Prod. Rep.

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Section: Formation Of Carbocyclesmentioning

confidence: 99%

Gold-catalyzed cyclization and cycloaddition in natural product synthesis

Lin,

Liu,

Luo

2024

Nat. Prod. Rep.

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An Overview of Syntheses of Salvinorin A and its Analogues

Tibouti,

Barriault

2024

ChemCatChem

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Salvinorin A is a powerful hallucinogen in humans, and a selective, high efficacy agonist of the kappa‐opioid receptor (κ‐OR). Salvinorin A is the first plant‐derived ligand with high selectivity for κ‐OR over other receptors, its structure is unrelated to any known opioid receptor ligands, even lacking any nitrogenous moieties. Mechanistically and pharmacologically, salvinorin A is distinct from other known hallucinogens in humans, making it the only selective κ‐OR ligand to gain wide‐spread interest outside of research. Structurally, salvinorin A bares a highly functionalized trans‐decalin core, containing two quaternary centers, and is fused to a δ‐lactone baring a furan moiety. Synthetic access of salvinorin A has been elusive due to a highly sensitive epimerizable center at carbon 8 (C8). All these features make salvinorin A a highly challenging synthetic target. With multiple synthetic efforts from around the world, only nine completed syntheses have been achieved to date. This review is intended to provide a look at the key strategies used to achieve the syntheses reported to date. We will summarize the efforts towards the syntheses of salvinorin A starting from Evans in 2007 to Barriault in 2023.

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Formal Synthesis of (±)‐Salvinorin A via Gold(I) Catalysis

Cited by 2 publications

References 26 publications

Gold-catalyzed cyclization and cycloaddition in natural product synthesis

Gold-catalyzed cyclization and cycloaddition in natural product synthesis

An Overview of Syntheses of Salvinorin A and its Analogues

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