Efficient synthesis of 2′,3′-dideoxynucleosides and 2′,3′-dideoxy C-nucleosides from D-glucosamine

Jung, Michael E.; Trifunovich, Ivan D.

doi:10.1016/s0040-4039(00)79561-x

Cited by 29 publications

(8 citation statements)

References 15 publications

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“…Next, substantial effort was put forth to reductively remove the acetoxy group, which proved quite challenging. Reductions of allylic acetates bearing oxygen on the vinylic carbon are precedented on cyclic systems, − but the corresponding reduction on linear substrates is rare and gives poor E/Z selectivity . Ultimately, we optimized nickel-catalyzed allylic reduction conditions reported by Yin, which afforded enol ether 9 .…”

Section: Resultsmentioning

confidence: 99%

Total Synthesis of (−)-Strictosidine and Interception of Aryne Natural Product Derivatives “Strictosidyne” and “Strictosamidyne”

et al. 2021

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Monoterpene indole alkaloids are a large class of natural products derived from a single biosynthetic precursor, strictosidine. We describe a synthetic approach to strictosidine that relies on a key facially selective Diels–Alder reaction between a glucosyl-modified alkene and an enal to set the C15–C20–C21 stereotriad. DFT calculations were used to examine the origin of stereoselectivity in this key step, wherein two of 16 possible isomers are predominantly formed. These calculations suggest the presence of a glucosyl unit, also inherent in the strictosidine structure, guides diastereoselectivity, with the reactive conformation of the vinyl glycoside dienophile being controlled by an exo-anomeric effect. (−)-Strictosidine was subsequently accessed using late-stage synthetic manipulations and an enzymatic Pictet–Spengler reaction. Several new natural product analogs were also accessed, including precursors to two unusual aryne natural product derivatives termed “strictosidyne” and “strictosamidyne”. These studies provide a strategy for accessing glycosylic natural products and a new platform to access monoterpene indole alkaloids and their derivatives.

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Section: Resultsmentioning

confidence: 99%

Total Synthesis of (−)-Strictosidine and Interception of Aryne Natural Product Derivatives “Strictosidyne” and “Strictosamidyne”

et al. 2021

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“…24 Due to the instability of the glycon in strong acid media, the ring-closure was performed in aqueous ammonium hydroxide solution, followed by tetrabutylammonium fluoride (TBAF) desilylation in THF, to yield the uridine and thymidine analogs 29 and 31 in 81 and 86 % yield, respectively, after two steps.…”

Section: Resultsmentioning

confidence: 99%

“…Finally, introduction of the nucleobase precursor was successfully achieved by quenching the intermediate isocyanate 20 with the lithium salts of the acrylic amides 24 and 25, leading to the uracil and thymidine precursors 26 and 27, which were obtained in 34 and 41% yield, respectively (Scheme 5). 24 Due to the instability of the glycon in strong acid media, the ring-closure was performed in aqueous ammonium hydroxide solution, followed by tetrabutylammonium fluoride (TBAF) desilylation in THF, to yield the uridine and thymidine analogues 29 and 31 in 81 and 86% yield, respectively, after two steps.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Synthesis of Conformationally North-Locked Pyrimidine Nucleosides Built on an Oxabicyclo[3.1.0]hexane Scaffold

Ludek

Márquez

2011

J. Org. Chem.

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Beginning with a known 3-oxabicyclo[3.1.0]hexane scaffold (I), the relocation of the fused cyclopropane ring bond and the shifting of the oxygen atom to an alternative location engendered a new 2-oxabicyclo[3.1.0]hexane template (II) that mimics more closely the tetrahydrofuran ring of conventional nucleosides. The synthesis of this new class of locked nucleosides involved a novel approach that required the isocyanate II (B = NCO) with a hydroxyl-protected scaffold as a pivotal intermediate that was obtained in eleven steps from a known dihydrofuran precursor. The completion of the nucleobases was successfully achieved by quenching the isocyanate with the lithium salts of the corresponding acrylic amides that led to the uracil and thymidine precursors in a single step. Ring closure of these intermediates led to the target, locked nucleosides. The anti-HIV activity of 29 (uridine analogue), 31 (thymidine analogue), and 34 (cytidine analogue) was explored in human osteosarcoma (HOS) cells or modified HOS cells (HOS-313) expressing the herpes simplex virus 1 thymidine kinase (HSV-1 TK). Only the cytidine analogue showed moderate activity in HOS-313 cells, which means that the compounds are not good substrates for the cellular kinases.

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“…[3][4][5][6][7][8][9][10] Indeed, the modern structural features of nucleosides are somewhat different from those present in poly-ribonucleotides RNA and DNA, [11] by means of variations in sugar, heterocyclic moieties and the various modes of attachments between the two major components (sugar and heterocycle). The literature of the new kinds of nucleosides is increasing and a lot of variations and kinds of nucleosides with dinuclear nucleosides [12,13] and others were also reported.…”

Section: Introductionmentioning

confidence: 99%

Computational Study of some Double Headed Acyclo-C-Nucleosides

Amara

Tchouar

Belaidi

2015

ILCPA

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ABSTRACT. In the present paper we have a focus in a study of theoretical characterization of three double headed acyclo-C-nucleosides, which are a recent target of experimental studies. The structural and electronic properties of double headed acyclo-C-nucleosides, 1,4-bis(3-mercapto-1H-1,2,4-triazol-5-yl)butane-1,2,3,4-tetrol, 1,4-bis(4-amino-5-mercapto-4H-1,2,4-triazol-3-yl)butane-1,2,3,4-tetrol and 5,5'-(1,2,3,4-tetrahydroxybutane-1,4-diyl)bis(1,3,4-oxadiazole-2(3H)-thione), have been investigated theoretically by performing semi-empirical molecular orbital, ab initio Hartree-Fock (HF) and Density Functional Theory (DFT) calculations. Geometries of the three molecules are optimized at the level of Austin Model 1 (AM1). The electronic properties and relative energies of the molecules have been calculated by HF and DFT in the ground state.

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Efficient synthesis of 2′,3′-dideoxynucleosides and 2′,3′-dideoxy C-nucleosides from D-glucosamine

Cited by 29 publications

References 15 publications

Total Synthesis of (−)-Strictosidine and Interception of Aryne Natural Product Derivatives “Strictosidyne” and “Strictosamidyne”

Total Synthesis of (−)-Strictosidine and Interception of Aryne Natural Product Derivatives “Strictosidyne” and “Strictosamidyne”

Synthesis of Conformationally North-Locked Pyrimidine Nucleosides Built on an Oxabicyclo[3.1.0]hexane Scaffold

Computational Study of some Double Headed Acyclo-C-Nucleosides

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