Bioinspired Synthesis of Alstoscholarinoids A and B

JACS Au, Год журнала: 2025, Номер 5(3), С. 1076 - 1082

Опубликована: Март 3, 2025

Biomimetic synthesis can be an attractive approach to access complex natural products by addressing challenging structural features through cascade reactions, which are inferred tangible biosynthetic hypotheses. In some instances, the originally proposed structure or path might revised synthesis. this communication we report a short and efficient bioinspired of Alstoscholarinoids A B, rearranged triterpenes from Alstonia scholaris tree. Salient include transannular aldol addition as well consisting Schenck–Ene reaction, Hock rearrangement, addition. This culminated in revision likely origin Alstoscholarinoid thorough exploration previously intermediates.

Язык: Английский

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Theoretical Investigation of the Mechanism of the Hock Rearrangement with InCl₃ as Catalyst**

ChemCatChem, Год журнала: 2023, Номер 15(16)

Опубликована: Июнь 13, 2023

Abstract The Hock rearrangement is an acid catalyzed reaction involving organic hydroperoxides and resulting in oxidative cleavage of adjacent C−C bonds. It has significant industrial applications, like the production phenol (cumene process), but it remains scarcely used synthesis. In addition, its detailed mechanism never been studied. Thus, we report herein a theoretical study rearrangement, using InCl 3 as Lewis catalyst. aim this work was to fully understand fundamental reaction, rationalize influence substrate electronic properties on outcome. Furthermore, structure active indium(III) catalyst interacting with peroxide investigated, revealing co‐existence several energetically close pathways. coordinated monomeric form emerges most compared dimeric species. However, show that 2 Cl 6 species are central catalytic cycle, primarily serving reservoir

Язык: Английский

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Tandem Hock and Friedel–Crafts reactions allowing an expedient synthesis of a cyclolignan-type scaffold

Beilstein Journal of Organic Chemistry, Год журнала: 2024, Номер 20, С. 162 - 169

Опубликована: Янв. 25, 2024

The Hock cleavage, which is compatible with tandem processes, was applied to the synthesis of 1-aryltetralines through a one-pot transformation from readily available benzyl(prenyl)malonate substrates. After photooxygenation prenyl moiety, resulting hydroperoxide directly engaged in cleavage by adding Lewis acid. presence an aromatic nucleophile reaction mixture and that benzyl moiety on substrate resulted Friedel–Crafts reactions form 1-aryltetraline products. These compounds share close analogy cyclolignan natural Experimental observations DFT study support involvement aldehyde intermediate during reactions, rather than oxocarbenium.

Язык: Английский

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Indium Triflate's Transformative Role in Modern Organic Synthesis: A Five‐Year Survey of Functionalization, Cyclization, and Multicomponent Reactions

ChemistrySelect, Год журнала: 2024, Номер 9(18)

Опубликована: Май 6, 2024

Abstract Indium triflate (In(OTf) 3 ) has proven to be a powerful and sustainable catalyst in the synthesis of modern organic compounds, enabling variety transformations such as functionalization, cyclization, multicomponent reactions. To provide insight into most recent methods applications, this study attempts comprehensive up‐to‐date summary these advances application indium synthesis, focusing on last five years literature. The opposed alternative indium(III) catalysts will main emphasis review, which cover developments through research articles reviews published between 2019 2023. This minireview make significant contribution existing literature by consolidating advancements use synthesis.

Язык: Английский

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Regioselectively electrochemical Csp3-H alkoxylation for functionalized indanone

Green Synthesis and Catalysis, Год журнала: 2024, Номер unknown

Опубликована: Дек. 1, 2024

Язык: Английский

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Tandem Hock and Friedel-Crafts reactions allowing an expedient synthesis of a cyclolignan-type scaffold

Опубликована: Ноя. 1, 2023

The Hock cleavage is an acid-catalyzed oxydative reaction involving allylic or benzylic hydroperoxides. Since it generates electrophilic oxocarbenium species, could be used in tandem processes the presence of nucleophiles. Here, starting from benzyl(prenyl)malonate substrates, prenyl moiety was first photooxygenated. resulting hydroperoxide directly engaged a by adding Lewis acid aromatic nucleophile to promote Friedel-Crafts reactions, also benzyl substrate. This sequence led one pot 1-aryltetraline products reminiscent cyclolignan natural product skeleton.

Язык: Английский

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Six-membered ring systems: With O and/or S atoms

Progress in heterocyclic chemistry, Год журнала: 2024, Номер unknown, С. 421 - 484

Опубликована: Янв. 1, 2024

Язык: Английский

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Available strategies for the synthesis of indenes for metal complex catalysis

Russian Chemical Bulletin, Год журнала: 2024, Номер 73(10), С. 2787 - 2800

Опубликована: Окт. 1, 2024

Язык: Английский

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