(π-Allyl)palladium coupling of 2-(tributylstannyl)cyclopent-2-enone for the synthesis of jasmonoid analogs

Parpal, Florencia; Pandolfi, Enrique; Heguaburu, Viviana

doi:10.1016/j.tetlet.2017.04.018

Cited by 3 publications

(10 citation statements)

References 29 publications

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“…However, structures that bear a methyl group at this position require high energy for coupling (60 and 80 °C). In contrast with previous reports, 13,14 we observed isomerization in both 7 and 8. On the one hand, compound 7 (obtained with a moderate yield of 55%) is isomerized in a 7:3 E/Z ratio.…”

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confidence: 99%

“…We observed isomerization in both 7 and 8, in contrast with previous reports. 13,14 Compound 7 (obtained with a moderate yield of 55%) was isomerized in a 7:3 E/Z ratio, whereas for the case of 8 (obtained in 42% yield), isomerization also occurred, delivering a 3:7 E/Z ratio. The presence of the methyl group in the -position relative to the ketone carbonyl group could explain the differences observed.…”

Section: Scheme 3 (-Allyl)palladium Cross-coupling For the Synthesis...mentioning

confidence: 99%

“…We recently developed a concise strategy for the synthesis of simplified jasmonoid derivatives. 13 This methodology employs a variant of the palladium-mediated Stille cross-coupling reaction 9 to attach an alkenyl side chain to a cyclopentenone core (Scheme 1).…”

Section: Paper Synthesismentioning

confidence: 99%

“…Flash column chromatography was performed by using 230-400 mesh silica gel 60. NMR spectra were recorded in CDCl 3 at room temperature on a Bruker AVANCE III 400 NMR spectrometer operating at 1 H and 13 C frequencies of 400.13 and 100.62 MHz, respectively, by using the residual solvent peak as an internal reference (7.26 ppm for 1 H and 77.0 ppm for 13 C). Chemical shifts () and coupling constants (J) are reported in ppm and Hz, respectively.…”

Section: Scheme 6 Hydrogenation Of Cinerone For the Synthesis Of Dihy...mentioning

confidence: 99%

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Synthesis of Pyrethroids and Jasmonoids through Palladium-Catalyzed Cross-Coupling Reactions

et al. 2022

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The synthesis of jasmone and related jasmonoids and pyrethroids is described. These types of compounds play a defensive role in plants, and share a cyclopentenone common core, with variations in its side chains. Jasmone, cinerone, allylrethrone and derivatives are synthesized through π-allyl palladium cross coupling of stannane derivatives. By selective hydrogenation dihydrojasmone and dihydrocinerone are also synthesized.

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confidence: 99%

Section: Scheme 3 (-Allyl)palladium Cross-coupling For the Synthesis...mentioning

confidence: 99%

Section: Paper Synthesismentioning

confidence: 99%

Section: Scheme 6 Hydrogenation Of Cinerone For the Synthesis Of Dihy...mentioning

confidence: 99%

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Synthesis of Pyrethroids and Jasmonoids through Palladium-Catalyzed Cross-Coupling Reactions

et al. 2022

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“…44 The sixteen-step strategy was based on two highly stereoselec- The retention of the geometry of the olefin in the allyl group was not always observed due to syn-anti isomerization of the -allylpalladium intermediate. 45 Scheme 34 Pd(0) coupling to obtain jasmonoid precursors 3 -Allylpalladium Complexes Generated from Dienes…”

Section: Total Synthesesmentioning

confidence: 99%

π-Allylpalladium Complexes in Synthesis: An Update

Parisotto¹,

Deagostino²

2019

Synthesis

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This review aims to summarize the development of the chemistry of π-allylpalladium complexes both as intermediates and catalysts/reagents between 2013 and early 2109. Major attention has been devoted to the synthetic aspect of these versatile intermediates.1 Introduction2 π-Allylpalladium Complexes Generated from Allyl Electrophiles2.1 Activated Allylic Compounds2.2 Unactivated Allylic Compounds: Allylic Alcohols and Hydrocarbons2.3 Total Syntheses3 π-Allylpalladium Complexes Generated from Dienes3.1 Conjugated Dienes3.2 Allenes4 π-Allylpalladium Complexes Exploited as Reactants and Precatalysts4.1 Allylpalladium-Catalyzed Dehydrogenation4.2 Allylpalladium-Catalyzed Synthesis of Alkenylboronic Esters4.3 Allylpalladium-Based Precatalysts5 Conclusions

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Synthesis and Anti-Proliferative Evaluation of Arctigenin Analogues with C-9′ Derivatisation

Paulin

Leung

Pilkington

et al. 2023

IJMS

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Dibenzylbutyrolactone lignans (DBLs) are a class of natural products with a wide variety of biological activities. Due to their potential for the development of human therapeutic agents, DBLs have been subjected to various SAR studies in order to optimise activity. Previous reports have mainly considered changes on the aromatic rings and at the benzylic carbons of the compounds, whilst the effects of substituents in the lactone, at the C-9′ position, have been relatively unexplored. This position has an unexploited potential for the development of novel dibenzyl butyrolactone derivatives, with previous preliminary findings revealing C-9′-hydroxymethyl analogues inducing programmed cell cycle death. Using the core structure of the bioactive natural product arctigenin, C-9′ derivatives were synthesised using various synthetic pathways and with prepared derivatives providing more potent anti-proliferative activity than the C-9′-hydroxymethyl lead compound.

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(π-Allyl)palladium coupling of 2-(tributylstannyl)cyclopent-2-enone for the synthesis of jasmonoid analogs

Cited by 3 publications

References 29 publications

Synthesis of Pyrethroids and Jasmonoids through Palladium-Catalyzed Cross-Coupling Reactions

Synthesis of Pyrethroids and Jasmonoids through Palladium-Catalyzed Cross-Coupling Reactions

π-Allylpalladium Complexes in Synthesis: An Update

Synthesis and Anti-Proliferative Evaluation of Arctigenin Analogues with C-9′ Derivatisation

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