A Convenient Large Scale Synthesis of Protected D-Ribonolactone From D-Ribose

Kaskar, Bashir; Heise, G. L.; Michalak, Ronald S.; Vishnuvajjala, B. R.

doi:10.1055/s-1990-27085

Cited by 65 publications

(41 citation statements)

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“…When the isopropylidene derivative 3, which retained the asymmetric carbons (C-4, C-7, C-8, C-9) in 2, was subjected successively to ozonolysis and NaBH 3 CN reduction, it afforded the isopropylidene of ribitol (4), [α] D 21 ϭ ϩ4.0 (c ϭ 0.35). Our ribitol (4) was directly compared with both its  and  epimers, prepared in our lab by the reported method, [15] and our synthesized  epimer was found to be identical in all respects ( 1 H NMR, 13 C NMR, and optical rotation) with the  isomer [16] derived from -ribose. Therefore, 4 has the (7R,8R,9S) absolute configuration, and so 2 has the (4R,7R,8R,9S) absolute configuration, and latrun- 13 C NMR spectroscopic data of the saccharide unit of 1 are also shown in Table 1 and Table 3.…”

Section: Resultsmentioning

confidence: 89%

“…The 1 H and 13 C NMR were in agreement with the literature data. [15] 2,3-O-Isopropylidene-L-ribitol (4): The isopropylidene derivative (6) was dissolved in a mixture of water (5 mL) and ethanol (1 mL) and, after the mixture had been cooled in an ice bath, a cold solution of sodium borohydride (0.3 mmol) in water (2 mL) was added dropwise. After the mixture had been stirred at room temperature for 15 h, the pH was adjusted to 5Ϫ6 with acetic acid (1.7 ).…”

Section: 3-o-isopropylidene-α/β-l-ribofuranose (6)mentioning

confidence: 99%

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Ten‐Membered Substituted Cyclic 2‐Oxecanone (Decalactone) Derivatives from Latrunculia corticata, a Red Sea Sponge

Řezanka

Dembitsky

2003

Eur J Org Chem

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Two novel glycosides, latrunculinosides A and B, containing substituted 2-oxecanones (decalactones) were isolated from Latrunculia corticata collected in the Gulf of Aqaba, Israel. They were characterized by spectroscopic methods, predominantly 1 H NMR, 13C NMR, MS, IR and UV, and by chemical degradation. Both glycosides contain unusual saccharides IntroductionMarine sponges belonging to the class Demospongiae have been the subject of extensive chemical and biological investigations. Numerous bioactive peptides have been isolated and identified in sponges, [1] and the continued interest of chemists in these marine organisms has yielded a large number of non-nitrogen-containing metabolites.[2] Sponges have also proven to be a rich source of a broad spectrum of natural products containing macrolactones, with fascinating structures and different biological activities.[3Ϫ5] The first compounds in this group were halicholactone and neohalicholactone, fatty acid metabolites found in the sponge Halichondria okadai, collected off the coast of Japan. [6,7] Similar compounds, didemnilactones A and B or neodidemnilactone, [8,9] were isolated from the colonial Didemnum moseleyi near the Japanese Islands and asciditrienolide A [10] from a marine tunicate (ascidian) Didemnum candidum. The correct structure of asciditrienolide was reported a few years later.[11]Here we report the isolation of the ten-membered ring lactonic glycosides latrunculinosides A and B from the sponge Latrunculia corticata. These compounds were assigned the structures 1 and 10 on the basis of chemical and spectroscopic methods. Results and DiscussionIn the course of our program devoted to the search for new compounds in marine animals [12,13] we found that ex- [a]

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Section: Resultsmentioning

confidence: 89%

Section: 3-o-isopropylidene-α/β-l-ribofuranose (6)mentioning

confidence: 99%

Ten‐Membered Substituted Cyclic 2‐Oxecanone (Decalactone) Derivatives from Latrunculia corticata, a Red Sea Sponge

Řezanka

Dembitsky

2003

Eur J Org Chem

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“…To a solution of 2,3-O-isopropylidene-D-ribofuranose 20 (8,6.243 g, 32.82 mmol) in anhydrous methanol (10 mL) was added indoline (7, 3.68 mL, 3.911g, 32.82 mmol) and reaction mixture was stirred under reflux for 5 h, then concentrated in vacuum and the obtained residue chromatographed on silica gel (150 g, hexane/acetone 3/1) to give 9 (6.1 g, 64%), as light yellow oil. Spectral data were identical with the described compound.…”

Section: -(23-o-isopropylidene-β-d-ribofuranosyl)indoline (9)mentioning

confidence: 99%

Synthesis and antiproliferative activity of 1-methoxy-, 1-(α-D-ribofuranosyl)- and 1-(β-D-ribofuranosyl)brassenin B

Čurillová¹,

Kutschy²,

Solčániová³

et al. 2008

Arkivoc

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Syntheses of indole phytoalexin 1-methoxybrassenin B and a linear synthesis of its nucleoside analogs 1-(α-D-ribofuranosyl)brassenin B and 1-(β-D-ribofuranosyl)brassenin B are reported from the corresponding 1-substituted indole-3-carboxaldehydes and carboxylic acids as key intermediates. Examination of the antiproliferative activity of synthesized compounds on human tumor cell lines Jurkat, CEM, CEM-VCR, MCF-7 and HeLa revealed the highest activity for 1-methoxybrassenin B, whereas activity of the nucleoside analogs decreased and appeared to be dependent on lipophilicity.

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“…The first two transformations involved selective acetonide protection of the cis-diol of the sugar, [14] followed by masking of the primary alcohol with various groups (60Ϫ80% over two steps, Scheme 1, R ϭ TBDMS, [14] trityl, [14] pivaloyl [15] ). The crux of the sequence was the Wittig reaction [16] followed by in situ DessϪMartin oxidation [17] of the resulting alcohol to afford the desired (Z)-α,β-unsaturated esters (Scheme 1).…”

Section: Synthesis Of Chiral Cyclobutanolsmentioning

confidence: 99%

“…(Ethoxycarbonylmethylene)triphenylphosphorane (181 mg, 0.50 mmol) was added to a solution of the protected ribose derivatives 2 [14,15] (0.41 mmol) in dry CH 2 Cl 2 (2 mL), and the reaction mixture was stirred at room temperature for 12 h. The mixture was diluted with CH 2 Cl 2 (2 mL), treated with DessϪMartin periodinane (209 mg, 0.50 mmol) and stirred at the same temperature for 12 h. The solvent was removed in vacuo, and the residue was purified by chromatography to afford the sugar derivatives 3.…”

Section: General Procedures For the Preparation Of αβ-Unsaturated Estmentioning

confidence: 99%

Highly Functionalised Cyclobutanols by Samarium(II) Iodide Induced Radical Cyclisations of Carbohydrate‐Derived Unsaturated Ketones

Williams¹,

Blann²

2004

Eur J Org Chem

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Certain carbohydrates have been found to be excellent precursors for the samarium diiodide‐mediated 4‐exo‐trig cyclisation reaction of their keto‐olefin derivatives, which were readily prepared in a few easy steps. The cyclisation was found to be stereoselective, affording cis products, the diastereoselective excesses of which were influenced by the nature of the protecting group employed at C5−O of the furanose sugar. The major chiral cyclobutane product of the cyclisation step was converted into an advanced intermediate for the synthesis of a nucleoside anti‐viral analogue. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)

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A Convenient Large Scale Synthesis of Protected D-Ribonolactone From D-Ribose

Cited by 65 publications

References 0 publications

Ten‐Membered Substituted Cyclic 2‐Oxecanone (Decalactone) Derivatives from Latrunculia corticata, a Red Sea Sponge

Ten‐Membered Substituted Cyclic 2‐Oxecanone (Decalactone) Derivatives from Latrunculia corticata, a Red Sea Sponge

Synthesis and antiproliferative activity of 1-methoxy-, 1-(α-D-ribofuranosyl)- and 1-(β-D-ribofuranosyl)brassenin B

Highly Functionalised Cyclobutanols by Samarium(II) Iodide Induced Radical Cyclisations of Carbohydrate‐Derived Unsaturated Ketones

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