Creating glycoside diversity through stereoselective carboboration of glycals DOI Creative Commons

Zhenpeng Shen,

Yue Yu, Donghai Wu

и другие.

Nature Communications, Год журнала: 2024, Номер 15(1)

Опубликована: Ноя. 23, 2024

Site-specific modification of glycosides to enhance or alter the physiological properties parent molecule has become a highly attractive strategy in drug development. However, creating glycoside building blocks with multiple diversifiable positions from readily available sugar precursors remains challenging task. Herein, we present regio- and stereoselective nickel-catalyzed carboboration glycals, which offers platform for generating diversity diverse C1 C2 potential. Specially, integration modifiable boronate group at position markedly amplifies versatility this approach, furnishing universal method swiftly rare sugars C2-site modifications through expedited downstream transformations. This demonstrates broad substrate scope tolerates various functional groups complex natural molecular architectures. Moreover, illustrate synthetic potential synthesis array analogs both products pharmaceuticals. Creating authors

Язык: Английский

Tetrafluoroethylation of Electron‐Rich Alkenyl Iodides Enabled by in situ Generation of Solvent‐Stabilized “Ligandless” CuCF2CF2H DOI

Cristina Maria Segovia,

Luana L. T. N. Porto,

Paula Casasús

и другие.

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер 366(12), С. 2684 - 2690

Опубликована: Апрель 23, 2024

Abstract In this study, we have developed a metal‐mediated synthetic method for incorporating the 1,1,2,2‐tetrafluoroethyl (CF 2 CF H) motif into unactivated, electron‐rich alkenyl iodides using cross‐coupling reactions. We discovered that stable Cu(CF H)(PPh Me) 3 complex, while unreactive with these substrates, serves as P‐ligated reservoir formation of solvent‐stabilized “ligandless” and reactive CuCF H species. This transformation occurs upon addition CuBr, which partially scavenges P‐ligand in form CuBr(PPh . The resulting situ generated solvent stabilized system significantly enhances reactivity particularly towards challenging substrates. advancement enables synthesis HCF ‐glycals, well nucleosides/nucleobases arenes.

Язык: Английский

Процитировано

2
Total synthesis of deinococcucins A–D and their isomeric derivatives via stereo- and regio-selective glycosylation: the discovery of a novel anti-angiogenic agent DOI

Honghui Lee,

Shihwa Seong,

Eun Seo Bae

и другие.

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(21), С. 6078 - 6082

Опубликована: Янв. 1, 2024

First total syntheses of deinococcucins A–D and their four new derivatives were achieved using stereo- regio-selective glycosylations as key reaction steps.

Язык: Английский

Процитировано

0
Creating glycoside diversity through stereoselective carboboration of glycals DOI Creative Commons

Zhenpeng Shen,

Yue Yu, Donghai Wu

и другие.

Nature Communications, Год журнала: 2024, Номер 15(1)

Опубликована: Ноя. 23, 2024

Site-specific modification of glycosides to enhance or alter the physiological properties parent molecule has become a highly attractive strategy in drug development. However, creating glycoside building blocks with multiple diversifiable positions from readily available sugar precursors remains challenging task. Herein, we present regio- and stereoselective nickel-catalyzed carboboration glycals, which offers platform for generating diversity diverse C1 C2 potential. Specially, integration modifiable boronate group at position markedly amplifies versatility this approach, furnishing universal method swiftly rare sugars C2-site modifications through expedited downstream transformations. This demonstrates broad substrate scope tolerates various functional groups complex natural molecular architectures. Moreover, illustrate synthetic potential synthesis array analogs both products pharmaceuticals. Creating authors

Язык: Английский

Процитировано

0