Stereocontrolled total synthesis of iminosugar 1,4-dideoxy-1,4-imino-D-iditol

Angelis, Martina De; Primitivo, Ludovica; Lucarini, C.; Agostinelli, Sonia; Sappino, Carla; Ricelli, Alessandra; Righi, Giuliana

doi:10.1016/j.carres.2020.108028

Cited by 8 publications

(4 citation statements)

References 23 publications

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“…Our synthesis starts with preparing the cis bromo derivative 4 obtained from readily available cis 1,4‐butenediol 2 . Thus, monoprotection of 1 by deprotonation with NaH in ether followed by equilibration to the monosodium salt followed by reaction with TBSCl in ether, afforded mono‐protected alcohol 3 in a 98% yield [28]. Conversion of 3 to bromide 4 was conducted by treatment with PPh 3 ‐NBS [29] to produce cis bromide 4 in 92% yield (Scheme 1).…”

Section: Resultsmentioning

confidence: 99%

“…To a solution of tert‐butyl N‐(diphenylmethylene)glycinate 4 (2.95 g, 10 mmol) in toluene/dichloromethane 3:1 (80 mL), O‐allyl‐N‐9‐ anthracenylmethylcinchonidium bromide 6 (0.565 g, 1 mmol) and allylic bromide 4 [28] (2.65 g, 10 mmol) added. The reaction mixture was cooled to 0°C and a 40% aqueous solution of sodium hydroxide (20 mL) was added.…”

Section: Methodsmentioning

confidence: 99%

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Synthesis of cyclic amino acid baikiain via asymmetric phase transfer catalysis

Espinoza‐Hicks

Chávez‐Flores

Galán

et al. 2023

Journal of Heterocyclic Chem

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The synthesis of the cyclic, naturally occurring amino acid baikiain from glycine and cis-1,4-butenediol is reported. The key step of the synthesis is an enantioselective phase transfer catalyzed allylation of the benzophenone imine of glycine t-butyl ester, catalyzed by a cinchonidine quaternary ammonium salt, which provided the allylated glycine in 82% yield and 80% e.e. Further deprotection and hydrolysis of the Schiff base followed by an intramolecular Mitsunobu ring closure reaction yielded the corresponding piperidine ring system in 77% yield, which by hydrolysis yielded baikiain hydrochloride in 36% overall yield. Hydrogenation of the double bond could provide access to (S)pipecolic acid, which is also an important chiral synthon.

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Synthesis of cyclic amino acid baikiain via asymmetric phase transfer catalysis

Espinoza‐Hicks

Chávez‐Flores

Galán

et al. 2023

Journal of Heterocyclic Chem

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“…Moreover, they are biologically active against several viral diseases, and they play an important role in glycosidase inhibition [ 111 ]. In 2020, Angelis et al [ 112 ] devised the total synthesis of iminosugar 1,4-dideoxy-1,4-imino-D-iditol in 11% overall yield by employing Sharpless asymmetric dihydroxylation. In the first step of synthesis, compound 247 was treated with sodium hydride, tert-butyldiphenylsilyl chloride and tetrahydrofuran to obtain compound 248, which over several steps synthesized compound 249 in 74% yield.…”

Section: Review Of the Literaturementioning

confidence: 99%

Sharpless Asymmetric Dihydroxylation: An Impressive Gadget for the Synthesis of Natural Products: A Review

et al. 2023

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Sharpless asymmetric dihydroxylation is an important reaction in the enantioselective synthesis of chiral vicinal diols that involves the treatment of alkene with osmium tetroxide along with optically active quinine ligand. Sharpless introduced this methodology after considering the importance of enantioselectivity in the total synthesis of medicinally important compounds. Vicinal diols, produced as a result of this reaction, act as intermediates in the synthesis of different naturally occurring compounds. Hence, Sharpless asymmetric dihydroxylation plays an important role in synthetic organic chemistry due to its undeniable contribution to the synthesis of biologically active organic compounds. This review emphasizes the significance of Sharpless asymmetric dihydroxylation in the total synthesis of various natural products, published since 2020.

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“…Most of the methods use carbohydrates as the chiral pool, which are transformed using reductive aminations or other transformation strategies . Alternatively, some asymmetric or biocatalysed approaches have been used . But, there are fewer reports on approaches where amino acids are used as the chiral pool for the synthesis of iminosugar derivatives …”

Section: Introductionmentioning

confidence: 99%

Amino Acid-Based Synthesis and Glycosidase Inhibition of Cyclopropane-Containing Iminosugars

et al. 2020

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Synthesis of four iminosugars fused to a cyclopropane ring is described using L-serine as the chiral pool. The key steps are large-scale preparation of an α,β-unsaturated piperidinone followed by completely stereoselective sulfur ylide cyclopropanation. Stereochemistry of compounds has been studied by nuclear Overhauser effect spectroscopy (NOESY) experiments and 1 H homonuclear decoupling to measure constant couplings. The activity of these compounds against different glycosidases has been evaluated. Although inhibition activity was low (compound 8a presents a (K i ) of 1.18 mM against βgalactosidase from Escherichia coli), interestingly, we found that compounds 8a and 8b increase the activity of neuraminidase from Vibrio cholerae up to 100%.

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Stereocontrolled total synthesis of iminosugar 1,4-dideoxy-1,4-imino-D-iditol

Cited by 8 publications

References 23 publications

Synthesis of cyclic amino acid baikiain via asymmetric phase transfer catalysis

Synthesis of cyclic amino acid baikiain via asymmetric phase transfer catalysis

Sharpless Asymmetric Dihydroxylation: An Impressive Gadget for the Synthesis of Natural Products: A Review

Amino Acid-Based Synthesis and Glycosidase Inhibition of Cyclopropane-Containing Iminosugars

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