Stereoselective synthesis of higher homologues of pantolactone from (R)-glyceraldehyde acetonide

Sanyal, Ishita; Barman, Piyali Deb; Banerjee, Anindyajit

doi:10.1016/j.tetlet.2014.12.065

Cited by 4 publications

(1 citation statement)

References 34 publications

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“…In 2014, a similar synthetic route to novel γ-substituted pantolactone homologues was designed based on a Sharpless asymmetric dihydroxylation of the enantiomeric alkene-ester derivative of (R)-glyceraldehyde acetonide 40 as the key step (Scheme 20). [72] Scheme 18. Asymmetric reduction of KPL by chiral NADPH model compounds Scheme 19.…”

Section: (R)-glyceraldehyde Acetonide As the Starting Materialsmentioning

confidence: 99%

Asymmetric Synthesis of Pantolactone: Recent Advances

Du,

Lv,

Liu

et al. 2023

Eur J Org Chem

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(R)‐Pantolactone, an intermediate in the syntheses of Vitamin B5 and coenzyme A, is an important chiral molecule often used as a food additive, chiral auxiliary, and chiral starting material for organic transformations. Enantioenriched pantolactones are predominantly produced by biological fermentation and chemical synthesis approaches. Herein, we present a review of recent developments in the asymmetric synthesis of pantolactone via different methods, and systematically summarize the characteristics and advantageous features of these strategies. Among the strategies discussed herein, the direct asymmetric catalysis of glyoxylate and isobutyraldehyde with small organocatalyst molecules has attracted growing attention owing to its good step‐economy, commercially available starting materials, absence of toxic reagents, mild reaction conditions, convenient operation, and low catalyst loading. These characteristics render the direct asymmetric route to pantolactone a particularly attractive procedure. This review provides valuable guidance for the design and synthesis of enantioenriched pantolactone and its analogs.

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Section: (R)-glyceraldehyde Acetonide As the Starting Materialsmentioning

confidence: 99%

Asymmetric Synthesis of Pantolactone: Recent Advances

Du,

Lv,

Liu

et al. 2023

Eur J Org Chem

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Chiral Hypervalent Iodine(III) Catalyst Promotes Highly Enantioselective Sulfonyl- and Phosphoryl-oxylactonizations

et al. 2016

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Biocatalytic Construction of Quaternary Centers by Aldol Addition of 3,3-Disubstituted 2-Oxoacid Derivatives to Aldehydes

et al. 2020

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The congested nature of quaternary carbons hinders their preparation, most notably when stereocontrol is required. Here we report a biocatalytic method for the creation of quaternary carbon centers with broad substrate scope, leading to different compound classes bearing this structural feature. The key step comprises the aldol addition of 3,3-disubstituted 2-oxoacids to aldehydes catalyzed by metal dependent 3-methyl-2-oxobutanoate hydroxymethyltransferase from E. coli (KPHMT) and variants thereof. The 3,3,3-trisubstituted 2-oxoacids thus produced were converted into 2-oxolactones and 3-hydroxy acids and directly to ulosonic acid derivatives, all bearing gem-dialkyl, gem-cycloalkyl, and spirocyclic quaternary centers. In addition, some of these reactions use a single enantiomer from racemic nucleophiles to afford stereopure quaternary carbons. The notable substrate tolerance and stereocontrol of these enzymes are indicative of their potential for the synthesis of structurally intricate molecules.

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Stereoselective synthesis of higher homologues of pantolactone from (R)-glyceraldehyde acetonide

Cited by 4 publications

References 34 publications

Asymmetric Synthesis of Pantolactone: Recent Advances

Asymmetric Synthesis of Pantolactone: Recent Advances

Chiral Hypervalent Iodine(III) Catalyst Promotes Highly Enantioselective Sulfonyl- and Phosphoryl-oxylactonizations

Biocatalytic Construction of Quaternary Centers by Aldol Addition of 3,3-Disubstituted 2-Oxoacid Derivatives to Aldehydes

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