Stereoselective total synthesis of Oxylipin from open chain gluco -configured building block

Borkar, Santosh R.; Aidhen, Indrapal Singh

doi:10.1016/j.carres.2017.03.002

Cited by 2 publications

(2 citation statements)

References 12 publications

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“…The deoxygenation was successfully preformed via the thiocabonylimidazolide 55 . Thiocarbonylimidazolides (iii) have also been used for the synthesis of tetrol derivatives with xylo configuration from d -1,5-gluconolactone, 106 the natural lipid oxylipin, 107 lemonose derivatives, 108 and deoxythreosyl nucleoside phosphonates, 109 among others. 110–115…”

Section: Deoxygenation Methodsmentioning

confidence: 99%

Deoxy sugars. General methods for carbohydrate deoxygenation and glycosidation

Marino

Bordoni

2022

Org. Biomol. Chem.

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Section: Deoxygenation Methodsmentioning

confidence: 99%

Deoxy sugars. General methods for carbohydrate deoxygenation and glycosidation

Marino

Bordoni

2022

Org. Biomol. Chem.

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“…Final deprotections completed the synthesis of the oxylipin 230 (Scheme 29). [134] Synthesis of D-xylo-1,2,3,4-alkane tetrols and L-xylo-1,2,3,4-alkane tetrols can be realized through the aldehyde 242 which was obtained through selective hydrolysis of the terminal isopropylidene protection, followed by oxidative cleavage. The orthogonality between the aldehyde and amide functionality reflects the potential of this key intermediate.…”

Section: Other Synthetic Pursuits Interfacing With Carbohydratesmentioning

confidence: 99%

Natural Products & Bioactivity Inspired Synthetic Pursuits Interfacing with Carbohydrates: Ongoing Journey with C‐Glycosides

Aidhen

Thoti

2021

The Chemical Record

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Natural products, remains the most important source for the discovery of new drugs for the treatment of human diseases. This has inspired the synthetic community to design and develop mimics of natural products either to answer important questions in biology or to explore their therapeutic potentials. Glycosides present themselves abundantly in nature, right from the cell surface receptors to natural products of any origin. The O-Glycosides are hydrolytically less stable compared to C-glycosides and this feature has presented a great opportunity for drug discovery. The discovery of Dapagliflozin, an SGLT inhibitor and C-glucoside, for the treatment of diabetes is one such example. Aryl acyl-anion chemistry has been explored for the synthesis of 2-deoxy-C-aryl furanoside/pyranoside/septanosides. Besides success, the studies have provided valuable insight into the natural propensities of the architectural framework for the cascade to furan derivatives. The aryl acyl-anion chemistry has also enabled the synthesis of biologically active diaryl heptanoids. Inspired from sucesss of Dapagliflozin, new analogues have been synthesized with pyridine and isocoumarin heterocycle as the proximal ring. C-glucosides of isoliquiritigenin have been synthesized for the first time and evaluated as an efficient aldose reductase inhibitor. The synthesis and evaluation of acyl-C-β-D-glucosides and benzyl-C-β-Dglucoside as glucose-uptake promoters has revealed promise in small molecules. The concept of building blocks has been used to obtain natural oxylipins, D-xylo and L-xylo-configured alkane tetrols and novel lipophilic ketones with erythro/threo configured trihydroxy polar head-group as possible anti-mycobacterial agents.

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Stereoselective total synthesis of Oxylipin from open chain gluco -configured building block

Cited by 2 publications

References 12 publications

Deoxy sugars. General methods for carbohydrate deoxygenation and glycosidation

Deoxy sugars. General methods for carbohydrate deoxygenation and glycosidation

Natural Products & Bioactivity Inspired Synthetic Pursuits Interfacing with Carbohydrates: Ongoing Journey with C‐Glycosides

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