Enantioselective Synthesis of a Furan Lignan (+)-Sylvone

Lee, Eun‐Hye; Bang, Jiyun; Kwon, Jisook; Yu, Chan‐Mo

doi:10.1021/acs.joc.5b01677

Cited by 12 publications

(11 citation statements)

References 55 publications

(26 reference statements)

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“…The importance of highly substituted tetrahydrofurans is indicated by the existence of numerous examples of pharmaceutically and biologically interesting tetrahydrofurans/tetrahydrofuran-containing complex molecules, including escitalopram, isosorbide mononitrate, naloxone, and sylvoneall of which possess at least one chiral center …”

Section: Introductionmentioning

confidence: 99%

Asymmetric Synthesis of Tetrahydrofurans through Palladium(0)-Catalyzed [3 + 2]-Cycloaddition of Vinylcyclopropanes with Ketenes

et al. 2019

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In this article we describe a new asymmetric synthesis of highly substituted tetrahydrofurans through a Pd(PPh3)4-catalyzed formal [3 + 2]-cycloaddition of donor-acceptor cyclopropanes and ketenes. The desired structural motif was formed in moderate to excellent yields (42-84% for 16 examples), with excellent Z:E isomer diastereoselectivity (≥19:1 for 16 examples), and with good to excellent enantioselectivity in all cases examined (83-97% ee for 6 examples). The synthetic utility of the products was illustrated by a number of diastereoselective transformations into reduced tetrahydrofurans and spirocyclic tetrahydrofuran-barbiturate derivatives.

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Section: Introductionmentioning

confidence: 99%

Asymmetric Synthesis of Tetrahydrofurans through Palladium(0)-Catalyzed [3 + 2]-Cycloaddition of Vinylcyclopropanes with Ketenes

et al. 2019

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“…Further transformations including a Michael addition provided the expected natural product (+)-Sylvone A ( 669 ) through a short 5-step reaction sequence. 383 …”

Section: Allenols In Natural Productsmentioning

confidence: 99%

Deciphering the Chameleonic Chemistry of Allenols: Breaking the Taboo of a Onetime Esoteric Functionality

2021

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The allene functionality has participated in one of the most exciting voyages in organic chemistry, from chemical curiosities to a recurring building block in modern organic chemistry. In the last decades, a special kind of allene, namely, allenol, has emerged. Allenols, formed by an allene moiety and a hydroxyl functional group with diverse connectivity, have become common building blocks for the synthesis of a wide range of structures and frequent motif in naturally occurring systems. The synergistic effect of the allene and hydroxyl functional groups enables allenols to be considered as a unique and sole functionality exhibiting a special reactivity. This Review summarizes the most significant contributions to the chemistry of allenols that appeared during the past decade, with emphasis on their synthesis, reactivity, and occurrence in natural products.

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“…Allenes bearing more complex substituents, particularly electron-withdrawing groups, have not been studied to any great extent in the context of metal ion-catalyzed cyclization to heterocycles. Wang studied allenyl silanes, and Lee examined allenyl esters in the context of gold- and copper-catalyzed cyclizations . It was only in 2015 that a silver-catalyzed cyclization of allenes bearing a group 15 electron-withdrawing group was published.…”

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confidence: 99%

“…Wang studied allenyl silanes, 14 and Lee examined allenyl esters in the context of gold-and copper-catalyzed cyclizations. 15 It was only in 2015 that a silver-catalyzed cyclization of allenes bearing a group 15 electron-withdrawing group was published. Thus, Christov reported that the reaction of phosphonate 1a and phosphine oxide 1b with 5 mol % of AgClO 4 in CH 2 Cl 2 at room temperature afforded dihydrofurans 2a and 2b in 83% and 85% yields, respectively, in under 1 h (Scheme 3).…”

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confidence: 99%