Divergent synthesis of various iminocyclitols from<scp>d</scp>-ribose

Petakamsetty, Ramu; Jain, Vipin; Majhi, Pankaj Kumar; Ramapanicker, Ramesh

doi:10.1039/c5ob01042j

Cited by 13 publications

(4 citation statements)

References 90 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The synthesis of pyrrolidines, including those with hydroxyalkyl substituents in the ring, has been recently reviewed . Some recent syntheses of this type of molecules have been reported …”

Section: Introductionmentioning

confidence: 99%

Synthesis of Enantiomeric Polyhydroxyalkylpyrrolidines from 1,3-Dipolar Cycloadducts. Evaluation as Inhibitors of a β-Galactofuranosidase

et al. 2016

View full text Add to dashboard Cite

Enantiomeric 2,3,4-tris(hydroxyalkyl)-5-phenylpyrrolidines have been synthesized from the major cycloadducts obtained by the 1,3-dipolar cycloaddition of sugar enones with azomethine ylides derived from natural amino acids. Reduction of the ketone carbonyl group of the cycloadducts, which possess a basic structure of bicyclic 6-(menthyloxy)hexahydropyrano[4,3-c]pyrrol-7(6H)one, afforded a number of pyrrolidine-based bicyclic systems. A sequence of reactions, which involved hydrolysis of the menthyloxy substituent, reduction, N-protection, and degradative oxidation, afforded varied pyrrolidine structures having diverse configurations and patterns of substitution; in particular, polyhydroxylated derivatives have been obtained. The unprotected products were isolated as pyrrolidinium trifluoroacetates. Because of the furanose-like nature of the target trihydroxyalkyl pyrrolidines, these molecules have been evaluated as inhibitors of the β-galactofuranosidase from Penicillium fellutanum. The compounds showed practically no inhibitory activity for concentration of pyrrolidines in the range of 0.1-1.6 mM.

show abstract

“…The synthesis of pyrrolidines, including those with hydroxyalkyl substituents in the ring, has been recently reviewed . Some recent syntheses of this type of molecules have been reported …”

Section: Introductionmentioning

confidence: 99%

Synthesis of Enantiomeric Polyhydroxyalkylpyrrolidines from 1,3-Dipolar Cycloadducts. Evaluation as Inhibitors of a β-Galactofuranosidase

et al. 2016

View full text Add to dashboard Cite

show abstract

“…cules, [32][33][34][35][36][37][38][39][40][41] we recently reported the synthesis of D-threosphinganine, L-erythro-sphinganine and (-)-spisulosine from an aldehyde derived from aspartic acid. 42 In the retrosynthetic analysis, it was anticipated that both bestatin and epibestatin could be synthesized from acid 9 using peptide coupling followed by deprotection of the Boc and MOM groups.…”

Section: Syn Openmentioning

confidence: 99%

Diastereoselective Synthesis of (–)-Bestatin, Epibestatin, Phebestin and (3S,4R)-4-Amino-3-hydroxy-5-phenylpentanoic Acid from an Aldehyde Derived from d-Phenylalanine

Jain

2019

SynOpen

Self Cite

View full text Add to dashboard Cite

A convenient and efficient method for the synthesis of (–)-bestatin, epibestatin, phebestin, and (3S,4R)-4-amino-3-hydroxy-5-phenylpentanoic acid is reported. The key step is a proline-catalyzed α-hydroxylation of an aldehyde derived from d-phenylalanine, which leads to incorporation of a hydroxyl group at the α-position of that aldehyde with good yield and very high diastereoselectivity. Bestatin and its diastereomer epibestatin are synthesized from the same starting material using the same sequence of reactions, except for proline as the catalyst. An O-MOM and Boc-protected amino acid, a common intermediate for bestatin, was coupled with a dipeptide, H-Val-Phe-OMe followed by global deprotection to yield phebestin. (3S,4R)-4-Amino-3-hydroxy-5-phenylpentanoic acid was also synthesized in eight steps from the same starting material. The reported synthetic route offers a general method for the synthesis of such types of compounds and their analogues by changing the proline catalyst and/or the starting material from d- to l-phenylalanine.

show abstract

“…Ramapanicker et al have developed a versatile and stereoselective strategy using proline-catalyzed α-amination as a key reaction to access this class of molecules. 50 Aldehydes 98, 99, 100, and 101, synthesized using chiral pool methods, have been successfully employed as starting materials for proline-catalyzed α-amination reaction to access five-, six-, and seven-membered azasugars after certain functional group transformation.…”

Section: Synthesis Of Diverse Iminocyclitols From D-ribosementioning

confidence: 99%

Proline-Catalyzed Asymmetric α-Amination in the Synthesis of Bioactive Molecules

Kumar

Sharma

2018

Synlett

View full text Add to dashboard Cite

The direct α-amination of carbonyl compounds using organocatalysts represents a powerful and atom-economical tool for asymmetric C–N bond formation. We describe a complete account of α-functionalization of carbonyl compounds, through iterative sequential α-aminoxylation/amination using electrophilic O and N sources, as well as sequential α-amination/HWE reaction for enantio- and diastereoselective synthesis of both syn- and anti-1,3-aminoalcohols and 1,3-diamines. Additionally this protocol is further extended for the easy construction of alkaloids such as indolizidine, pyrrolizidine, and quinolizidine fused-ring systems just by tuning the chain length of the aldehyde used as a starting material. This methodology provides further scope to extrapolate it for a variety of naturally occurring hydroxylated monocyclic and fused bicyclic pyrrolidine and piperidine based alkaloids such as lentiginosine, epi-lentiginosine, dihydroxypyrrolizidine, (+)-deoxoprosophylline and (–)-deoxoprosopinine alkaloids. Furthermore, we have also uncovered proline-catalyzed anti-selectivity for the synthesis of 1,2-amino alcohols in α-amination of aldehyde and one-pot indium-mediated Barbier type allylation of α-hydrazino aldehydes to accomplish the total synthesis of clavaminols, sphinganine and spisulosine with reduced number of steps and with high overall yields.1 Introduction2 Application in the Total Synthesis of Alkaloids3 Conclusion

show abstract

Divergent synthesis of various iminocyclitols fromd-ribose

Cited by 13 publications

References 90 publications

Synthesis of Enantiomeric Polyhydroxyalkylpyrrolidines from 1,3-Dipolar Cycloadducts. Evaluation as Inhibitors of a β-Galactofuranosidase

Synthesis of Enantiomeric Polyhydroxyalkylpyrrolidines from 1,3-Dipolar Cycloadducts. Evaluation as Inhibitors of a β-Galactofuranosidase

Diastereoselective Synthesis of (–)-Bestatin, Epibestatin, Phebestin and (3S,4R)-4-Amino-3-hydroxy-5-phenylpentanoic Acid from an Aldehyde Derived from d-Phenylalanine

Proline-Catalyzed Asymmetric α-Amination in the Synthesis of Bioactive Molecules

Contact Info

Product

Resources

About