A Combined Tamaru Allylation/Olefin Cross-Metathesis Approach for the Total Syntheses of (±)-Paniculidine B, (±)-Paniculidine C, and 2-Methylcarbazole

Tseng, Yi-Lun; Liang, Min-Chieh; Chen, I‐Chia; Wu, Yen‐Ku

doi:10.1055/s-0036-1591739

Cited by 6 publications

References 13 publications

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Alkene Cross‐Metathesis Reactions

et al. 2021

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This chapter describes olefin cross‐metathesis (CM) reactions catalyzed by ruthenium, molybdenum, and tungsten complexes and surveys the literature from 1993 through 2020. Cross‐metathesis has been applied to the synthesis of a wide range of functionalized alkenes, including natural and biologically active products. Due to its simplicity and inherit atom economy, CM has found applications in the preparation of fine chemicals and various building blocks, and in transformations of biomass. Tandem reactions involving CM as the key step are also reviewed. Examples discussed in this chapter serve to illustrate how the reactivity of alkene substrates in CM depends on the presence of functional groups and steric congestion in the proximity of the reacting double bonds. A discussion of the mechanism of olefin metathesis is also included.

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Alkene Cross‐Metathesis Reactions

et al. 2021

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An Apparent Umpolung Reactivity of Indole through [Au]‐Catalysed Cyclisation and Lewis‐Acid‐Mediated Allylation

Shinde

Ramana

2020

Chemistry A European J

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The sequential functionalization of indole C2 and C3 in an umpolung fashion was executed with a predesigned substrate and choice of reagents. The developed method comprises gold‐catalysed alkynol cycloisomerisation/intramolecular addition of C2 of indole and subsequent BF3⋅OEt2‐mediated regioselective C3 allylation, resulting in the synthesis of the functionalized indoloisoquinolinone scaffold. The reaction involves 5‐endo‐alkynol cycloisomerisation and the dearomative addition of indole C2 to the intermediate oxocarbenium cation, which results in two equilibrating fused and spiropentacyclic intermediates, which upon treatment with allyl silane in the presence of BF3⋅OEt2, undergo selective indole C3 allylation. Other nucleophiles, such as hydride, azide and indole, were also found to be compatible with this process.

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Flow Friedel–Crafts alkylation of 1‐adamantanol with arenes using HO‐SAS as an immobilized acid catalyst

Kasakado

Hyodo

Furuta

et al. 2020

J Chinese Chemical Soc

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In this communication flow Friedel-Crafts alkylation was studied using hydroxy-substituted sulfonic acid-functionalized silica as a catalyst and 1-adamantanol as a model substrate. The reaction of 1-adamantanol (1a) with toluene (2a) proceeded well with 5 min of residence time at 120 C to give good yield of 1-tolyladamantane (3a) as a 1:9 mixture of meta and para isomers. When the flow synthesis was carried out over 2.5 hr of running time, the collected five fractions contain the product 3a in 97-92% yields, suggesting the durability of the catalyst.

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A Combined Tamaru Allylation/Olefin Cross-Metathesis Approach for the Total Syntheses of (±)-Paniculidine B, (±)-Paniculidine C, and 2-Methylcarbazole

Cited by 6 publications

References 13 publications

Alkene Cross‐Metathesis Reactions

Alkene Cross‐Metathesis Reactions

An Apparent Umpolung Reactivity of Indole through [Au]‐Catalysed Cyclisation and Lewis‐Acid‐Mediated Allylation

Flow Friedel–Crafts alkylation of 1‐adamantanol with arenes using HO‐SAS as an immobilized acid catalyst

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