Acid-catalyzed isomerization of caryophyllene in the presence of SiO2 and Al2O3 impregnated with sulfuric acid

Romanenko, E. P.; Ткачев, А. В.

doi:10.1007/s11172-018-2179-3

Russ Chem Bull

2018

DOI: 10.1007/s11172-018-2179-3

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Acid-catalyzed isomerization of caryophyllene in the presence of SiO2 and Al2O3 impregnated with sulfuric acid

E. P. Romanenko

А. В. Ткачев

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Cited by 2 publications

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“…Commercial vendors provide β-caryophyllene ( 4 ) at a low price, comparable with limonene or pinene. Nevertheless, the use of caryophyllene ( 4 ) as a starting material to obtain other natural compounds is limited to a biomimetic total synthesis of meroterpenoids − and rearrangement studies to access more complex terpene structures. − …”

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confidence: 99%

A Concise Bioinspired Semisynthesis of Rumphellaones A–C and Their C-8 Epimers from β-Caryophyllene

et al. 2020

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The first semisynthetic route toward rumphellaones B (2) and C (3) and their C-8 epimers as well as the shortest synthesis of rumphellaone A (1) and its C-8 epimer from the most accessible sesquiterpene, β-caryophyllene (4), is presented. Synthetic routes involved caryophyllonic acid as a key intermediate, which was converted to rumphellaone A (and epimer) via acid-catalyzed lactonization and rumphellaone C (and epimer) using one-pot epoxidation–lactonization. Rumphellaone B (2) and its epimer were obtained from rumphellaone A (1) and its epimer, respectively, using Saegusa–Ito oxidation. The absolute configuration at C-8 was confirmed by single-crystal X-ray analysis of rumphellaone B (2) and an acylated derivative of rumphellaone C.

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A Concise Bioinspired Semisynthesis of Rumphellaones A–C and Their C-8 Epimers from β-Caryophyllene

et al. 2020

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Heteropoly acid-catalyzed β-caryophyllene chemical transformations: Synthesis route of value-added commercial products from components found in biorenewable resources

Silva

Vieira

Rocha

2023

Molecular Catalysis

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Acid-catalyzed isomerization of caryophyllene in the presence of SiO2 and Al2O3 impregnated with sulfuric acid

Cited by 2 publications

References 27 publications

A Concise Bioinspired Semisynthesis of Rumphellaones A–C and Their C-8 Epimers from β-Caryophyllene

A Concise Bioinspired Semisynthesis of Rumphellaones A–C and Their C-8 Epimers from β-Caryophyllene

Heteropoly acid-catalyzed β-caryophyllene chemical transformations: Synthesis route of value-added commercial products from components found in biorenewable resources

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