A Fast and Convenient Procedure for the Acetylation of Alcohols

Martínez-Pascual, Roxana; Viñas-Bravo, Omar; Meza‐Reyes, Socorro; Iglesias-Arteaga, Martı́n A.; Sandoval‐Ramírez, Jesús

doi:10.1081/scc-200043272

Cited by 7 publications

(6 citation statements)

References 8 publications

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“…Ramirez et al reported that the acetylation of secondary and tertiary alcohols could be readily achieved by treatment with acetic anhydride and BF 3 ·OEt 2 at room temperature in just a few seconds . We found this procedure to be both clean and straightforward without major side reactions.…”

Section: Resultsmentioning

confidence: 55%

“…18 We found this procedure to be both clean and straightforward without major side reactions. These conditions were compatible with the sensitive manzamine molecule bearing several functional groups, whereas commonly utilized basic media were expected to decompose the alkaloid.…”

Section: Resultsmentioning

confidence: 91%

“…Ramirez et al reported that the acetylation of secondary and tertiary alcohols could be readily achieved by treatment with acetic anhydride and BF 3 • OEt 2 at room temperature in just a few seconds. 18 We found this procedure to be both clean and straightforward without major side reactions. These conditions were compatible with the sensitive manzamine molecule bearing several functional groups, whereas commonly utilized basic media were expected to decompose the alkaloid.…”

Section: Resultsmentioning

confidence: 91%

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Kinetic Studies and Bioactivity of Potential Manzamine Prodrugs

et al. 2008

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The manzamines represent a class of marine natural products that show considerable promise in the control of malaria but generate GI distress in rodents when administered orally in high doses. In an effort to generate manzamine prodrugs with improved antimalarial activity and reduced GI toxicity, we prepared acetylated 8-hydroxymanzamine A analogues including 8-acetoxymanzamine A (3) and 8,12-diacetoxymanzamine A (4), and 8-methoxymanzamine A (5) beginning with 8-hydroxymanzamine A (2). The semisynthetic analogues were assayed for antimalarial and antimicrobial activities, cytotoxicity, and biological and chemical stability. Due to gradual hydrolysis of the ester group, application of monoacetate 3 as an antimalarial prodrug was investigated. The in vitro and in vivo bioassays show that acetylated analogues exhibit significant antimalarial activity (IC50(3) 9.6–30 ng/mL), which are comparable to the parent molecule; however the monoaceate 3 was shown to actually produce higher toxicity at 30 mg/kg when administered orally.

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Section: Resultsmentioning

confidence: 55%

Section: Resultsmentioning

confidence: 91%

Section: Resultsmentioning

confidence: 91%

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Kinetic Studies and Bioactivity of Potential Manzamine Prodrugs

et al. 2008

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“…31 However, without control of the reaction time, the formation of an array of acetate species occurred.…”

Section: Semisynthesis Of Kahalalide F Analoguesmentioning

confidence: 99%

Lysosome and HER3 (ErbB3) Selective Anticancer Agent Kahalalide F: Semisynthetic Modifications and Antifungal Lead-Exploration Studies

et al. 2007

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Kahalalide F (1) shows remarkable antitumor activity against different carcinomas and has recently completed phase I clinical trials and is being evaluated in phase II clinical studies. The antifungal activity of this molecule has not been thoroughly investigated. In this report, we focused on acetylation and oxidation of the secondary alcohol of threonine, as well as reductive alkylation of the primary amine of ornithine, and each product was evaluated for improvements in antifungal activity. 1 and analogues do not exhibit antimalarial, antileishmania, or antibacterial activity; however, the antifungal activity against different strains of fungi was particularly significant. This series of compounds was highly active against Fusarium spp., which represents an opportunistic infection in humans and plants. The in vitro cytotoxicity for the new analogues of 1 was evaluated in the NCI 60 cell panel. Analogue 5 exhibited enhanced potency in several human cancer cell lines relative to 1.

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“…Various organic and inorganic catalysts have been employed. The highest number of references deal with the use of Lewis acids, 2 amongst them: Mg(NTf 2 ) 2 , 3 Mg(HSO 4 ) 2 , 4 Al(OTf) 3 , 5 Sc(OTf) 3 , 6 lithium salts, 7 distannoxane derivatives, 8 Er(OTf) 3 , 9 ErCl 3 , 10 SbCl 3 , 11 NbCl 5 , 12 InCl 3 , 13 TaCl 5 , 14 CoCl 2 , 15 tin(IV) porphyrin derivatives, 16 La(NO 3 ) 3 , 17 lanthanide(III) tosylates, 18 copper salts, 19 bismuth oxide perchlorate, 20 zirconium salts, 21 cerium salts, 22 a Mn(III) complex, 23 Gd(OTf) 3 , 24 Al(HSO 4 ) 3 , 25 BF 3 •OEt 2 , 26 cobalt polyoxometalate, 27 bismuth salts, 28 and silica derivatives. 29 Protic acid catalysis is less common, both under homogeneous and heterogeneous conditions.…”

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confidence: 99%

o-Benzenedisulfonimide as a Soft, Efficient, and Recyclable Catalyst for the Acylation of Alcohols, Phenols, and Thiols under Solvent-Free Conditions: Advantages and Limitations

Barbero¹,

Cadamuro²,

Dughera³

et al. 2008

Synthesis

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o-Benzenedisulfonimide turns out to be a highly efficient Brønsted acid catalyst for the acylation of a number of alcohols, phenols, and thiols under a metal-and solvent-free procedure; reaction conditions are mild and yields very good. After the workup, the catalyst can be easily recovered and purified, ready to be reused, with economic and ecological advantages.Functional group protection is often essential in organic synthesis, so many methods and procedures of both protection and deprotection are continuously proposed in the literature. Alcohols, phenols, and thiols are routinely protected by acylation and, despite the high number of known procedures, new and more efficient methodologies are still in demand. The most commonly used reagents are acid anhydrides, although in the reaction one acyl moiety is lost, and acetic or benzoic anhydrides are the most frequently employed. The reaction with primary and secondary alcohols normally requires the presence of a suitable catalyst, whereas a strong base catalyst is needed for hindered tertiary alcohols. 1Taking into consideration only the literature concerning the acylation of alcohols, phenols, thiols, and amines with acid anhydrides, the number of recent reports is astonishing, including the use of both homogeneous and heterogeneous catalysts. Most methods employ solvent-free conditions, room temperature (for acetylation with Ac 2 O) or heating (for other anhydrides, less commonly used), in the presence of Brønsted or Lewis acid catalysts.Various organic and inorganic catalysts have been employed. The highest number of references deal with the use of Lewis acids, 2 amongst them: Mg(NTf 2 ) 2 , 3 Mg(HSO 4 ) 2 , 4 Al(OTf) 3 , 5 Sc(OTf) 3 , 6 lithium salts, 7 distannoxane derivatives, 8 Er(OTf) 3 , 9 ErCl 3 , 10 SbCl 3 , 11 NbCl 5 , 12 InCl 3 , 13 TaCl 5 , 14 CoCl 2 , 15 tin(IV) porphyrin derivatives, 16 La(NO 3 ) 3 , 17 lanthanide(III) tosylates, 18 copper salts, 19 bismuth oxide perchlorate, 20 zirconium salts, 21 cerium salts, 22 a Mn(III) complex, 23 Gd(OTf) 3 , 24 Al(HSO 4 ) 3 , 25 BF 3 ·OEt 2 , 26 cobalt polyoxometalate, 27 bismuth salts, 28 and silica derivatives. 29Protic acid catalysis is less common, both under homogeneous and heterogeneous conditions. 4-Toluenesulfonic acid (alcohols; toluene, reflux), 30 phosphomolybdic acid (alcohols, phenols, and amines; neat, r.t., long reaction times), 31 3-nitrobenzeneboronic acid (alcohols; r.t.), 32 and sulfamic acid (alcohols and phenols) 33 have been used.Under heterogeneous conditions, solid acids such as montmorillonite, 34 zeolites, 35 zirconia, 36 Nafion-H, 37 macroporous metal oxides, 38 solid superacid, 39 and heteropolyacids, 40 have also been exploited for acetylation or acylation (in a few cases) of alcohols, phenols, thiols, and amines, under solvent-free conditions and at reflux or room temperature. In other examples of heterogeneous catalysis for O-and N-acetylation, the protic acid catalyst is supported on a high-surface insoluble inorganic or organic support, such as sulfated zirconia 41a or MoO 3...

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A Fast and Convenient Procedure for the Acetylation of Alcohols

Cited by 7 publications

References 8 publications

Kinetic Studies and Bioactivity of Potential Manzamine Prodrugs

Kinetic Studies and Bioactivity of Potential Manzamine Prodrugs

Lysosome and HER3 (ErbB3) Selective Anticancer Agent Kahalalide F: Semisynthetic Modifications and Antifungal Lead-Exploration Studies

o-Benzenedisulfonimide as a Soft, Efficient, and Recyclable Catalyst for the Acylation of Alcohols, Phenols, and Thiols under Solvent-Free Conditions: Advantages and Limitations

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