Stereoselective sulfoxide directed reduction of 1,2-diketo-derivatives to enantiomerically pure syn and anti 1,2-diols

Solladié, Guy; Hanquet, Gilles; Rolland, Catherine

doi:10.1016/s0040-4039(97)01300-2

Cited by 25 publications

(4 citation statements)

References 7 publications

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“…While zinc borohydride [18] offered perfect anti-selectivity (syn/anti = 1:99), side reactions led to a poor yield of only 30 % after HPLC purification. The same lack of chemoselectivity was also observed with DIBALH/zinc iodide [19] and other reagent systems. Carrying out the reduction with lithium aluminum hydride and lithium iodide, [20] 19 could finally be obtained, after silylation, with good overall yield and acceptable anti-selectivity.…”

Section: L-diginose and L-oleandrosesupporting

confidence: 71%

Alkoxyallene‐Based De Novo Synthesis of Rare Deoxy Sugars: New Routes to L‐Cymarose, L‐Sarmentose, L‐Diginose and L‐Oleandrose

Brasholz

Reißig

2009

Eur J Org Chem

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Section: L-diginose and L-oleandrosesupporting

confidence: 71%

Alkoxyallene‐Based De Novo Synthesis of Rare Deoxy Sugars: New Routes to L‐Cymarose, L‐Sarmentose, L‐Diginose and L‐Oleandrose

Brasholz

Reißig

2009

Eur J Org Chem

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“…It was found that addition of a Lewis acid modified the yield and selectivity in the DIBAL-H reduction of β-silyloxy γ-ketosulfoxide. 363 Of the Lewis acids tested, Yb(OTf) 3 resulted in high selectivity for syn product and ZnI 2 for anti product (Table 166). DIBAL-H was used for highly stereoselective reduction of γ-ketosulfoxide.…”

Section: Reductionmentioning

confidence: 99%

Rare-Earth Metal Triflates in Organic Synthesis

et al. 2002

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“…According to the carbon chemical shifts of these methyl groups of 6 , overlapping at 27.0 ppm, the relative stereochemistry of the 1,2-diol was proposed as threo . [21,22,23]. …”

Section: Resultsmentioning

confidence: 99%

Erylusamides: Novel Atypical Glycolipids from Erylus cf. deficiens

et al. 2016

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Among marine organisms, sponges are the richest sources of pharmacologically-active compounds. Stemming from a previous lead discovery program that gathered a comprehensive library of organic extracts of marine sponges from the off-shore region of Portugal, crude extracts of Erylus cf. deficiens collected in the Gorringe Bank (Atlantic Ocean) were tested in the innovative high throughput screening (HTS) assay for inhibitors of indoleamine 2,3-dioxygenase (IDO) and showed activity. Bioassay guided fractionation of the dichloromethane extract led to the isolation of four new glycolipids, named erylusamide A–D. The structures of the isolated compounds were established by 1D and 2D nuclear magnetic resonance (NMR) spectroscopy, high-resolution electrospray ionization mass spectrometry (HR-ESI-MS) and chemical derivatization. The metabolites shared a pentasaccharide moiety constituted by unusual highly acetylated d-glucose moieties as well as d-xylose and d-galactose. The aglycones were unprecedented long chain dihydroxyketo amides. Erylusamides A, B and D differ in the length of the hydrocarbon chain, while erylusamide C is a structural isomer of erylusamide B.

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Stereoselective sulfoxide directed reduction of 1,2-diketo-derivatives to enantiomerically pure syn and anti 1,2-diols

Cited by 25 publications

References 7 publications

Alkoxyallene‐Based De Novo Synthesis of Rare Deoxy Sugars: New Routes to L‐Cymarose, L‐Sarmentose, L‐Diginose and L‐Oleandrose

Alkoxyallene‐Based De Novo Synthesis of Rare Deoxy Sugars: New Routes to L‐Cymarose, L‐Sarmentose, L‐Diginose and L‐Oleandrose

Rare-Earth Metal Triflates in Organic Synthesis

Erylusamides: Novel Atypical Glycolipids from Erylus cf. deficiens

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