Synthesis of nortropane alkaloid calystegine B2 from methyl α-d-xylopyranoside

Underlin, Emilie Nørmølle; Jensen, Henrik H.

doi:10.1016/j.carres.2018.12.002

Cited by 4 publications

(6 citation statements)

References 37 publications

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“…Column chromatography (20% EtOAc in cyclohexane) of the residue gave a second batch of the title compound, which when added to the first batch of crystals gave 8 (14.7 g, 45% over three steps) as a mixture of anomers. All analytical data for 8 were in agreement with those previously reported. , …”

Section: Experimental Sectionsupporting

confidence: 91%

“…All analytical data for 8 were in agreement with those previously reported. 52 Compound 15 was prepared using previously reported methods. 55 Compound 13 was prepared using previously reported methods.…”

Section: 34-tri-o-benzyl-d-xylopyranose (8)mentioning

confidence: 99%

“…Compound 8 was prepared using previously reported methods. ,, d -Xylose (11.7 g, 0.078 mol) was dissolved in MeOH (150 mL), to which DOWEX 50WX8 (H + ) (11.7 g) was added, and the mixture was stirred at reflux for 12 h. The mixture was filtered, and the solvents were removed under reduced pressure. The residue was redissolved in DMF (200 mL) and cooled to 0 °C.…”

Section: Experimental Sectionmentioning

confidence: 99%

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Flow Chemistry for Synthesis of 2-(C-Glycosyl)acetates from Pyranoses via Tandem Wittig and Michael Reactions

Bennett,

Murphy

2024

Org. Process Res. Dev.

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C-Glycosyl compounds (C-glycosides) are a class of saccharide derivatives with improved stability over their O-linked counterparts. This paper reports the synthesis of several trans-2-(C-glycosyl)acetates via a tandem Wittig−Michael reaction from pyranoses (cyclic hemiacetals) using continuous flow processing, which gave improvements compared to reactions conducted in round-bottom flasks. Products were isolated in yields of >60% from reactions of benzyl-protected xylopyranoses, glucopyranoses, and galactopyranoses at higher temperatures and pressures, which were superior to yields from batch procedures. A two-step procedure involving the Wittig reaction followed by Michael reaction (intramolecular oxa-Michael) of the unsaturated ester obtained in the presence of DBU was developed. Reactions of protected mannopyranose gave low yields in corresponding reactions in flow due to competing C-2 epimerization.

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Section: Experimental Sectionsupporting

confidence: 91%

Section: 34-tri-o-benzyl-d-xylopyranose (8)mentioning

confidence: 99%

Section: Experimental Sectionmentioning

confidence: 99%

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Flow Chemistry for Synthesis of 2-(C-Glycosyl)acetates from Pyranoses via Tandem Wittig and Michael Reactions

Bennett,

Murphy

2024

Org. Process Res. Dev.

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Section: Ring‐closing Metathesis (Rcm)mentioning

confidence: 99%

“…The group of Jensen fruitfully revealed the synthesis calystegine B 2 422 (Scheme 58), a nortropane alkaloid showing selective glycosidase inhibition profile with the involvement of the metathesis protocol. [239] The DMP-oxidation of an alcohol 418 produced an aldehyde, which was later treated with vinyl magnesium bromide to obtain an allylic alcohol 419. Another DMP-oxidation of 419 afforded an enone 420, which effectively underwent to ring closing metathesis with HG-II catalyst and delivered an α,β-unsaturated cycloheptanone 421 in 63% yield.…”

Section: Total Synthesis Of Natural Products Based On Rcmmentioning

confidence: 99%

Metathesis Reactions in Natural Product Fragments and Total Syntheses

et al. 2022

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The passion of total‐ and fragments syntheses of natural products always remained one of the top priorities among the synthetic chemists worldwide. Due their curiosity toward the complexity of molecules of living nature and their endeavour to imitate them in laboratory; limitless arrays of natural products have been extracted, architecturally‐elucidated, synthesized, and chronicled by utilizing various synthetic methodologies in different fashions. Frequently, the synthesis of complex natural products proceed with inscrutable synthetic challenges, which can be circumvented either by modification of previously developed synthetic methods or by formulating a new one. In this way, a myriad of powerful synthetic reactions have been developed since the genesis of the logic of chemical synthesis. Amongst them, metathesis tactics discovered unexpectedly in the 1950s (Nobel Prize in 2005), have incredibly influenced and changed the landscape of the art of the total and formal synthesis in the last three A. H. Hoveyda, A. R. Zhugralin, me abruptly as compared to other developed transformations or their modified forms. In this particular review article, we envisioned to report a comprehensive detail of the metathetic tools involved in both total and fragments synthesis of natural products in the years 2018 and 2019 along with an overview of 2017.

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Glycosides, Synthesis and Characterization

Brito-Arias

2022

Synthesis and Characterization of Glycosides

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Synthesis of nortropane alkaloid calystegine B2 from methyl α-d-xylopyranoside

Cited by 4 publications

References 37 publications

Flow Chemistry for Synthesis of 2-(C-Glycosyl)acetates from Pyranoses via Tandem Wittig and Michael Reactions

Flow Chemistry for Synthesis of 2-(C-Glycosyl)acetates from Pyranoses via Tandem Wittig and Michael Reactions

Metathesis Reactions in Natural Product Fragments and Total Syntheses

Glycosides, Synthesis and Characterization

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