Diastereoselective syntheses of 1-deoxyhomonojirimycin and two new 1,5,6-trideoxy-1,5-iminoheptitols with d-allo- and l-talo-configuration

Bouc, Géraldine Le; Thomassigny, Christine; Greck, Christine

doi:10.1016/j.tetasy.2006.07.022

Cited by 13 publications

(6 citation statements)

References 39 publications

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“…[35] Selective deprotection of the exocyclic acetonide in compound 35 gave access to ad iol, which was oxidatively cleaved to afford aldehyde 36. [35] Selective deprotection of the exocyclic acetonide in compound 35 gave access to ad iol, which was oxidatively cleaved to afford aldehyde 36.…”

Section: Sato (2013) -(+ +)-Pancratistatin (1)mentioning

confidence: 99%

“…d-Glucose was converted to protected d-glucofuranose 35 after treatment with dry acetone and bromodimethylsulfonium bromide,f ollowed by silyl protection according to published procedures (Scheme 8). [35] Selective deprotection of the exocyclic acetonide in compound 35 gave access to ad iol, which was oxidatively cleaved to afford aldehyde 36. TheH enry reaction [36] of aldehyde 36 with nitromethane, mesylation of the resulting alcohol, and the elimination of the mesylate under basic conditions produced nitroolefin 37.The authors exploited the Michael acceptor capacity of compound 37 in its reaction with the aryl cuprate generated from 38 with Mg/CuI/TMSCl in THF.O nly one enantiomer (Michael adduct 39)was formed in this step.Model reactions suggested that replacement of the tert-butyldimethylsilyl (TBDMS) functionality with methyl group gave rise to am ixture of isomers,h ence the role of the TBDMS functionality was significant in the stereoselectivity of the reaction.…”

Section: Sato (2013) -(+ +)-Pancratistatin (1)mentioning

confidence: 99%

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Synthesis of Amaryllidaceae Constituents and Unnatural Derivatives

et al. 2016

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This update covers the syntheses of Amaryllidaceae alkaloids since the publication of the last major review in 2008. A short summary of past syntheses and their step count is provided for the major constituents; pancratistatin, 7-deoxypancratistatin, narciclasine, lycoricidine, lycorine, and for other natural constituents, as well as for unnatural derivatives. Discussion of biological activities is provided for unnatural derivatives. Future prospects and further developments in this area are covered at the end of the review. The literature is covered to the end of August 2015.

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Section: Sato (2013) -(+ +)-Pancratistatin (1)mentioning

confidence: 99%

Section: Sato (2013) -(+ +)-Pancratistatin (1)mentioning

confidence: 99%

Synthesis of Amaryllidaceae Constituents and Unnatural Derivatives

et al. 2016

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“…IR spectra were recorded with FT-IR as a thin film or in Nujol mull or using KBr pellets. 1 H NMR (300 MHz) and 13 C NMR (75 MHz) spectra were recorded using CDCl 3 and/or D 2 O as solvent(s) with reference to TMS as an internal standard. Elemental analyses were carried out with a C,H-analyzer.…”

Section: Figure 3 Lowest Energy Conformations Of Dinucleoside 14 and mentioning

confidence: 99%

“…12 Hydrolysis of the major acetate 2a gave 3 wherein; the stereochemical 5-(R) assignment was established by desilylation in 3 and by matching the spectral and analytical data with the reported compound. 13 Mesylation of 3 using mesyl chloride and triethylamine in dichloromethane followed by sodium azide treatment in N,N-dimethylformamide gave 5-(S)-azido compound 4. 14 One pot acetolysis of the 1,2-acetonide and acetylation of the 2-OH afforded the glycosyl donor which on modified Vorbruggen glycosylation 15 with silylated thymine in the presence of trimethylsilyl triflate gave β-nucleoside 5.…”

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Studies toward Oxyacetamide-Linked RNA Analogues: Synthesis and Conformation of a Modified Dinucleoside

et al. 2012

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A new oxyacetamide-modified dinucleoside with 5′-(S) chirality, a hydrophobic 5′-C-(2-methoxyethyl) group, and a 2′-Omethyl group was synthesized from D-glucose. This dinucleoside showed a helical structure based on CD and NMR spectroscopy. The sugar puckering at the 5′ and 3′ ends were found to be 'S'-and 'N'-types, respectively. These results were substantiated by ab initio density functional theory.

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A Concise Total Synthesis of (+)‐Pancratistatin from D‐Glucose Featuring the Henry Reaction

et al. 2013

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Pancratistatin (PST, Scheme 1) is a natural compound that was first isolated [1] from Spider Lily, a plant native to Hawaii that belongs to the Amaryllidaceae family. As well as antiviral and antiparasitic activities, PST has very strong antitumor activity. [2] Furthermore, PST can act as an antitumor secondary metabolite that can induce apoptosis in tumor cells by targeting their mitochondria while leaving normal cells unaffected. [3] Therefore, as well as being a challenging compound to synthetic chemists, a facile large-scale synthesis of PST and its analogs would be of great importance in pharmaceutical sciences. [4,5] However, despite many attempts to synthesize PST and its analogs (various epimers and/or deoxy derivatives, Scheme 1), [4g,h,j] a practical and scalable synthesis of from readily available starting compounds has remained elusive.We have been engaged in the total syntheses of naturally occurring branched-chain cyclitol compounds, such as cyclophellitol, mytillitol, laminitol, and (À)-tetrodotoxin (TTX), [6] by using d-glucose as the starting material. Herein, we describe the concise stereoselective total synthesis of (+)-PST from d-glucose, which features both inter-and intramolecular Henry reactions [7] (nitroaldol reactions) as key transformations. As shown in the retrosynthetic plan (Scheme 2), the key intermediate C-aryl nitrocyclitol B can be prepared from D by the intramolecular [a] Assoc. Scheme 1. Pancratistatin (PST) and its related compounds. Scheme 2. Retrosynthetic analysis of (+)-PST from d-glucose featuring an intramolecular Henry reaction.

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Diastereoselective syntheses of 1-deoxyhomonojirimycin and two new 1,5,6-trideoxy-1,5-iminoheptitols with d-allo- and l-talo-configuration

Cited by 13 publications

References 39 publications

Synthesis of Amaryllidaceae Constituents and Unnatural Derivatives

Synthesis of Amaryllidaceae Constituents and Unnatural Derivatives

Studies toward Oxyacetamide-Linked RNA Analogues: Synthesis and Conformation of a Modified Dinucleoside

A Concise Total Synthesis of (+)‐Pancratistatin from D‐Glucose Featuring the Henry Reaction

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