Stereoselective synthesis of 5-monoalkyl and 5,5-dialkylsubstituted noviose derivatives

Periers, Anne-Marie; Laurin, Patrick; Benedetti, Yannick; Lachaud, Sylvette; Ferroud, Didier; Iltis, Alain; Haesslein, Jean‐Luc; Klich, Michel; L’Hermite, Guillaume; Musicki, Branislav

doi:10.1016/s0040-4039(99)02177-2

Cited by 25 publications

(16 citation statements)

References 15 publications

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“…3) are coumarin antibiotics of natural origin, which are inhibitors of DNA girase, and have a broad spectrum towards Gram-positive bacteria, including methicilin resistant strains of staphylococci species [228,255].…”

Section: Antimicrobial and Molluscicidalmentioning

confidence: 99%

Simple Coumarins and Analogues in Medicinal Chemistry: Occurrence, Synthesis and Biological Activity

Borges¹,

Roleira²,

Milhazes³

et al. 2005

CMC

890

458

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Coumarins, also known as benzopyrones, are present in remarkable amounts in plants, although their presence has also been detected in microorganisms and animal sources. The structural diversity found in this family of compounds led to the division into different categories, from simple coumarins to many other kinds of policyclic coumarins, such as furocoumarins and pyranocoumarins. Simple coumarins and analogues are a large class of compounds that have attracted their interest for a long time due to their biological activities: they have shown to be useful as antitumoural, anti-HIV agents and as CNS-active compounds. Furthermore, they have been reported to have multiple biological activities (anticoagulant, anti-inflammatory), although all these properties have not been evaluated systematically. In addition, their enzyme inhibition properties, antimicrobial and antioxidant activities are other foremost topics of this field of research. The present work is to survey the information published or abstracted from 1990 till 2003, which is mainly related to the occurrence, synthesis and biological importance of simple coumarins and some analogues, such as biscoumarins and triscoumarins. Data are also highlighted, concerning the development of new synthetic strategies that could help in drug design and in the work on SAR or QSAR.

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Section: Antimicrobial and Molluscicidalmentioning

confidence: 99%

Simple Coumarins and Analogues in Medicinal Chemistry: Occurrence, Synthesis and Biological Activity

Borges¹,

Roleira²,

Milhazes³

et al. 2005

CMC

890

458

View full text Add to dashboard Cite

show abstract

“…Although 1 and 2 have frequently been used for the introduction of the benzyl group into a carbohydrate molecule [12–18], the benzyl→ o -tolyl rearrangement has, to the best of our knowledge, only been reported once. In this regard, Panigot and Curley [19] showed that the reaction of 1 with 2,3,4,6-tetra- O -acetyl-α-D-glucopyranosyl bromide (or chloride) produced a 3:1 mixture of 2-(β-D-glucopyranosyl)toluene and (β-D-glucopyranosyl)phenylmethane isolated as the corresponding 2,3,4,6-tetra- O -acetates.…”

Section: Resultsmentioning

confidence: 99%

Reaction of selected carbohydrate aldehydes with benzylmagnesium halides: benzyl versus o-tolyl rearrangement

Bella

Steiner

Langer

et al. 2014

Beilstein J. Org. Chem.

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SummaryThe Grignard reaction of 2,3-O-isopropylidene-α-D-lyxo-pentodialdo-1,4-furanoside and benzylmagnesium chloride (or bromide) afforded a non-separable mixture of diastereomeric benzyl carbinols and diastereomeric o-tolyl carbinols. The latter resulted from an unexpected benzyl to o-tolyl rearrangement. The proportion of benzyl versus o-tolyl derivatives depended on the reaction conditions. Benzylmagnesium chloride afforded predominantly o-tolyl carbinols while the application of benzylmagnesium bromide led preferably to the o-tolyl carbinols only when used in excess or at higher temperatures. The structures of the benzyl and o-tolyl derivatives were confirmed unambiguously by NMR spectral data and X-ray crystallographic analysis of their 5-ketone analogues obtained by oxidation of the corresponding mixture of diastereomeric carbinols. A possible mechanism for the Grignard reaction leading to the benzyl→o-tolyl rearrangement is also proposed.

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“…This offers the additional advantage that structural modifications of the glycosidic part of natural or unnatural glycoconjugates can be accomplished more conveniently. [17][18][19][20][21][22][23] Noviose analogues have been obtained, for instance, from l-arabinose by incorporation of alkyl substituents other than methyl at the C-5 position, [24] or in de novo approaches by the introduction of amino groups at C-3. [8,9] Alternative routes rely on the modification of other common carbohydrates [10][11][12][13][14][15][16] or are de novo syntheses.…”

Section: Introductionmentioning

confidence: 99%

Metathesis‐Based De Novo Synthesis of Noviose

Schmidt

Hauke

2014

Eur J Org Chem

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The rare carbohydrate L‐(+)‐noviose was synthesized from enantiomerically pure L‐lactate. The configuration at C‐4 was established by diastereoselective nucleophilic addition to an in‐situ‐generated lactaldehyde. The resulting homoallylic alcohol was further transformed into a set of ring‐closing metathesis (RCM) precursors. These compounds were converted into noviose in few steps using RCM and RCM–allylic‐oxidation sequences.

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Stereoselective synthesis of 5-monoalkyl and 5,5-dialkylsubstituted noviose derivatives

Cited by 25 publications

References 15 publications

Simple Coumarins and Analogues in Medicinal Chemistry: Occurrence, Synthesis and Biological Activity

Simple Coumarins and Analogues in Medicinal Chemistry: Occurrence, Synthesis and Biological Activity

Reaction of selected carbohydrate aldehydes with benzylmagnesium halides: benzyl versus o-tolyl rearrangement

Metathesis‐Based De Novo Synthesis of Noviose

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