Novel Synthesis of Castanospermine and 1-Epicastanospermine

Cronin, Linda; Murphy, Paul V.

doi:10.1021/ol0508577

Cited by 46 publications

(9 citation statements)

References 17 publications

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“…Oxidations of primary alcohol groups in glycopyranosides by TPAP/NMO/ PMS/CH 2 Cl 2 were used en route to the antiviral agents castanospermine and 1-epicastanospermine [338].…”

Section: Primary Alcohol Groups In Pyranosesmentioning

confidence: 99%

“…2.13, 2.4.2.1), used in a synthesis of D-allose [329]. Oxidations of primary alcohol groups in glycopyranosides by TPAP/NMO/PMS/CH 2 Cl 2 was used en route to the antiviral agents castanospermine and 1-epicastanospermine [338]. Methyl 4,6-O-benzylidene-2-deoxy-a-L-arabino-hexopyranoside was converted by RuO 2 /aq.…”

Section: Syntheses Of Carbohydrate Natural Products/ Pharmaceuticalsmentioning

confidence: 99%

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Oxidation of Alcohols, Carbohydrates and Diols

Griffith

2009

Catalysis by Metal Complexes

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This is one of the most important classes of oxidation effected by Ru complexes, particularly by RuO 4 , [RuO 4 ] − , [RuO 4 ] 2− and RuCl 2 (PPh 3 ) 3 , though in fact most Ru oxidants effect these transformations. The chapter covers oxidation of primary alcohols to aldehydes (section 2.1), and to carboxylic acids (2.2), and of secondary alcohols to ketones (2.3). Oxidation of primary and secondary alcohol functionalities in carbohydrates (sugars) is dealt with in section 2.4, then oxidation of diols and polyols to lactones and acids (2.5). Finally there is a short section on miscellaneous alcohol oxidations in section 2.6.In this chapter the first of the two most important categories of oxidations catalysed by Ru complexes (the other being alkene and alkyne oxidations in Chapter 3) are considered. The approach in this and subsequent chapters differs from that of Chapter 1, concentrating here on the substrate rather than on the oxidant. The text is divided into the categories of alcohols and their oxidations. There are summaries in section 2.3.6 of systems of limited applicability which are mentioned only in Chapter 1, and in section 2.3.7 of large-scale (>1 g) oxidations.The first oxidations of alcohols by stoicheiometric RuO 4 /H 2 O were reported in 1958, of primary alcohols to aldehydes or carboxylic acids and secondary alcohols to ketones [1]. The first Ru-catalysed oxidation of an alcohol was reported in 1965 when Parikh and Jones used RuO 2 /aq. Na(IO 4 )/CCl 4 1 ( Table 2.3) [2] to oxidise secondary alcohol groups in carbohydrates.Oxidation of alcohols is the most frequently reviewed topic for Ru-catalysed oxidations [3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18][19][20]. Mechanisms of alcohol oxidation by Ru complexes have been reviewed [21].

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“…Oxidations of primary alcohol groups in glycopyranosides by TPAP/NMO/ PMS/CH 2 Cl 2 were used en route to the antiviral agents castanospermine and 1-epicastanospermine [338].…”

Section: Primary Alcohol Groups In Pyranosesmentioning

confidence: 99%

Section: Syntheses Of Carbohydrate Natural Products/ Pharmaceuticalsmentioning

confidence: 99%

Oxidation of Alcohols, Carbohydrates and Diols

Griffith

2009

Catalysis by Metal Complexes

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“…[31] This approach was used in a general synthesis of iminosugars, [32] and this has included the development of a synthesis of castanospermine and 1-epicastanospermine. [33] Scheme 1. Synthesis of 1-deoxymannojirimycin.…”

Section: Synthesis Of Non-peptide Peptidomimeticsmentioning

confidence: 99%

Peptidomimetics, Glycomimetics and Scaffolds from Carbohydrate Building Blocks

Murphy

2007

Eur J Org Chem

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Saccharides, due to their high density of functional groups and availability as chiral building blocks are scaffolds for bioactive compound discovery. Pyranosides and iminosugar‐based peptidomimetics have been synthesised as ligands for somatostatin receptors and HIV protease. The synthesis of polyhydroxylated macrolides related to natural products and cyclophanes has been achieved from carbohydrate fragments with a view to investigation of their potential as scaffolds. In addition, the trajectory of aromatic systems grafted to saccharides have been studied and this has led to the synthesis of probes for the study of carbohydrate protein interactions. These compounds include geometrically diverse bivalent glycomimetics derived from scaffolds that are hybrids of sugars and aromatic groups. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

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“…In the first step, hydrolysis of the oxazolidinone group was carried out under basic conditions with aqueous NaOH in methanol at reflux. Then, in the second step, hydrogenolysis of the resulting dibenzylated derivative in an acidic medium [26] with Pd(OH) 2 as the catalyst afforded the expected adenophorine as its hydrochloride.…”

Section: Stereoselective Addition Of the Secondary Hydroxy Groupsmentioning

confidence: 99%