Synthesis of new echinocandin derivatives via a diol-keto transposition

Aszodi, J.; Fauveau, Patrick; Melon-Manguer, Dominique; Ehlers, Eberhard; Schio, Laurent

doi:10.1016/s0040-4039(02)00422-7

Cited by 5 publications

(1 citation statement)

References 14 publications

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“…The pinacol rearrangement of vic -diols has been known since 1860 . This transformation involving a dehydration and skeletal rearrangement is one of the earliest documented Wagner−Meerwein rearrangements in carbocation chemistry and has been used as a key step in organic synthesis . The intermediate cations are usually generated under Lewis or Bronsted acid conditions, which often result in regioisomeric mixtures of ketones and aldehydes when unsymmetrical diols are used (eq 1).…”

Section: Introductionmentioning

confidence: 99%

Photochemical Pinacol Rearrangements of Unsymmetrical Diols

et al. 2004

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The photochemical pinacol reaction of a series of nonsymmetrical 9-fluorenyl-substituted vic-diols was investigated and compared with their acid-catalyzed thermal reaction. Unlike the thermal reaction, the radiation-induced processes involve only fluorenyl cations, as is reflected in differences of product distribution between the two reactions. From the product studies, substituent migratory aptitudes are reversed in the photochemical process, suggesting that kinetic control takes place under neutral conditions unlike the acid-catalyzed thermal reactions. The presence of fluorenyl cation intermediates and their lifetimes were established by laser flash spectroscopy studies.

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Section: Introductionmentioning

confidence: 99%

Photochemical Pinacol Rearrangements of Unsymmetrical Diols

et al. 2004

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Echinocandins: production and applications

Emri

Majoros

Tóth

et al. 2013

Appl Microbiol Biotechnol

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The first echinocandin-type antimycotic (echinocandin B) was discovered in the 1970s. It was followed by the isolation of more than 20 natural echinocandins. These cyclic lipo-hexapeptides are biosynthesized on non-ribosomal peptide synthase complexes by different ascomycota fungi. They have a unique mechanism of action; as non-competitive inhibitors of β-1,3-glucan synthase complex they target the fungal cell wall. Results of the structure-activity relationship experiments let us develop semisynthetic derivatives with improved properties. Three cyclic lipohiexapeptides (caspofungin, micafungin and anidulafungin) are currently approved for use in clinics. As they show good fungicidal (Candida spp.) or fungistatic (Aspergillus spp.) activity against the most important human pathogenic fungi including azole-resistant strains, they are an important addition to the antifungal armamentarium. Some evidence of acquired resistance against echinocandins has been detected among Candida glabrata strains in recent years, which enhanced the importance of data collected on the mechanism of acquired resistance developing against the echinocandins. In this review, we show the structural diversity of natural echinocandins, and we summarize the emerging data on their mode of action, biosynthesis and industrial production. Their clinical significance as well as the mechanism of natural and acquired resistance is also discussed.

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Cyclic, Modified and Conjugated Peptides

Davies

2006

Amino Acids, Peptides and Proteins

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Synthesis of new echinocandin derivatives via a diol-keto transposition

Cited by 5 publications

References 14 publications

Photochemical Pinacol Rearrangements of Unsymmetrical Diols

Photochemical Pinacol Rearrangements of Unsymmetrical Diols

Echinocandins: production and applications

Cyclic, Modified and Conjugated Peptides

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