- A Short Total Synthesis of (+/-)-Gephyrotoxin-223AB
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(+/-)-Gephyrotoxin-223AB has been synthesized from 2-carbomethoxycyclopentanone in nine steps by a route utilizing the stereoselective homolytic cyclization of an alkenyl-substituted N-chloropiperidine.
- Broka, Chris A.,Eng, Kan K.
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- BiCl3-Facilitated removal of methoxymethyl-ether/ester derivatives and DFT study of -O-C-O- bond cleavage
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A simple method for the cleavage of methoxymethyl (MOM)-ether and ester derivatives using bismuth trichloride (BiCl3) is described. The alkyl, alkenyl, alkynyl, benzyl and anthracene MOM ether derivatives, as well as MOM esters of both aliphatic and aromatic carboxylic acids, were deprotected in good yields. To better understand the molecular roles of BiCl3and water for MOM cleavage, two possible binding pathways were investigated using the density functional theory (DFT) method. The theoretical results indicate the differential initial binding site preferences of phenolic and alcoholic MOM substrates to the Bi atom and suggest that water plays a key role in facilitating the cleavage of the MOM group.
- Pacherille, Angela,Tuga, Beza,Hallooman, Dhanashree,Dos Reis, Isaac,Vermette, Mélodie,Issack, Bilkiss B.,Rhyman, Lydia,Ramasami, Ponnadurai,Sunasee, Rajesh
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supporting information
p. 7109 - 7116
(2021/05/03)
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- Tert-Butyl Nitrite Promoted Oxidative Intermolecular Sulfonamination of Alkynes to Synthesize Substituted Sulfonyl Pyrroles from the Alkynylamines and Sulfinic Acids
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tert-Butyl nitrite promoted oxidative intermolecular sulfonamination of alkynes to synthesize substituted sulfonyl pyrroles from the alkynylamines and sulfinic acids via tandem addition/cyclization was developed. This reaction is performed well by employing tert-butyl nitrite as the oxidant, and various substituted sulfonyl pyrroles are formed in moderate to good yields with no requirement of metal catalysis.
- Qi, Zhenjie,Jiang, Yong,Wang, Yanyan,Yan, Rulong
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supporting information
p. 8636 - 8644
(2018/06/18)
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- Cu-Catalyzed Tandem Aerobic Oxidative Cyclization for the Synthesis of 3,3′-Bipyrroles from the Homopropargylic Amines
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A Cu-catalyzed method for the synthesis of 3,3′-bipyrroles from homopropargylic amines through tandem aerobic oxidative cyclization involving the formation of C-C bond has been developed. The features of this reaction are a small number of Cu catalysis and simple starting substrates. Moreover, this procedure exhibits good functional group tolerance and a series of 3,3′-bipyrroles derivatives are obtained in moderate to good yields.
- Qi, Zhenjie,Jiang, Yong,Yuan, Bingxiang,Niu, Yanning,Yan, Rulong
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supporting information
p. 5048 - 5052
(2018/08/24)
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- A mild method for the deprotection of tetrahydropyranyl (THP) ethers catalyzed by iron(III) tosylate
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A mild method for the deprotection of THP ethers catalyzed by iron(III) tosylate (2.0 mol %) in CH3OH has been developed. Iron(III) tosylate, Fe(OTs)3·6H2O, is a commercially available solid that is inexpensive, noncorrosive, and easy to handle. The room temperature reaction conditions make this method attractive for deprotection of a range of THP ethers.
- Bockman, Matthew R.,Angeles, Veronica V.,Martino, Julia M.,Vagadia, Purav P.,Mohan, Ram S.
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experimental part
p. 6939 - 6941
(2012/02/05)
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- M -Terphenyl Ethers, a new hydroxy protecting group cleavable under reductive single electron transfer reaction conditions
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m-Terphenyl ethers and, to a lesser extent, 2,6-dimethoxyphenyl ethers, were tested as protected hydroxy derivatives under a variety of reaction conditions. These ethers underwent regioselective cleavage of the aromatic C(1)-O bond under reductive SET reaction conditions using alkali metals in tetrahydrofuran at room temperature. This deprotective procedure was efficiently realized in the presence of several other functional groups, including an acetal, a phenyl alkyl ether, an unprotected alcohol, and carbon-carbon double and triple bonds. Furthermore, m-terphenyl ethers proved stable under different reaction conditions, including acidic hydrolysis and formation and/or employment of different organometallic reagents. Georg Thieme Verlag Stuttgart · New York.
- Azzena, Ugo,Mocci, Sarah,Pisano, Luisa
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experimental part
p. 1575 - 1580
(2011/06/24)
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- A mild and chemoselective method for the deprotection of tert-butyldimethylsilyl (TBDMS) ethers using iron(III) tosylate as a catalyst
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The most common method for the deprotection of TBDMS ethers utilizes stoichiometric amounts of tetrabutylammonium fluoride, n-Bu4N+F- (TBAF), which is highly corrosive and toxic. We have developed a mild and chemoselective method for the deprotection of TBDMS, TES, and TIPS ethers using iron(III) tosylate as a catalyst. Phenolic TBDMS ethers, TBDPS ethers and the BOC group are not affected under these conditions. Iron(III) tosylate is an inexpensive, commercially available, and non-corrosive reagent.
- Bothwell, Jason M.,Angeles, Veronica V.,Carolan, James P.,Olson, Margaret E.,Mohan, Ram S.
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supporting information; experimental part
p. 1056 - 1058
(2010/04/05)
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- Synthesis of anacardic acids, 6-[8(Z),11(Z)-pentadecadienyl]salicylic acid and 6-[8(Z),11(Z),14-pentadecatrienyl]salicylic acid
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11-Chloro-3-methoxy-2-undecenal was synthesized from 8-bromooctanol, and an annelation reaction with this aldehyde and ethyl acetoacetate proceeded to give the ethyl 6-(8-chlorooctyl)salicylate. Ethyl 6-(8-chlorooctyl)salicylate was converted to ethyl 6-(7-formylheptyl)-2-methoxybenzoate through the iodide after protection of the phenolic hydroxyl group. Finally, the Wittig reaction with the aldehyde and triphenylphosphonium iodides in the presence of BuLi gave the methoxybenzoates, and then treatments of these methoxybenzoates with BBr3 in CH2Cl2 and 10% NaOH in ethanol gave 6-[8(Z),11(Z)-pentadecadienyl]salicylic acid (anacardic acid 3) and 6-[8(Z),11(Z),14-pentadecatrienyl]salicylic acid (anacardic acid 4) which were isolated from plants of the anacardiaceae.
- Satoh,Takeuchi,Nishimura,Ohta,Tobinaga
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- COMPOUNDS WITH GREEN PLANT FRAGRANCE. IV. SUBSTITUTED CIS-3-ALKEN-1-OLS
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Syntheses are reported for leaf alcohol analogs, namely, substituted cis-3-alken-1-ols.Many of these compounds have green plant fragrance similar to that of a leaf alcohol standard (cis-3-hexen-1-ol).
- Vasil'ev, A. A.,Cherkaev, G. V.,Nikitina, M. A.
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p. 220 - 225
(2007/10/02)
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- INSECT PHEROMONES AND THEIR ANALOGS. XIII. SYNTHESIS OF DODEC-8E-ENYL AND DODEC-8Z-ENYL ACETATES - COMPONENTS OF THE SEX PHEROMONES OF Grapholitha funebrana AND Grapholitha molesta
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A new route is proposed for the synthesis of dodec-8E-enyl and dodec-8Z-enyl acetates which is based on the reaction of the Grignard reagent from the readily accessible 1-bromo-5-(1-ethoxyethoxy)pentane with 1-bromohept-3-yne - the bromide obtained from product of the β-hydroxyethylation of pent-1-yne with 2-chloroethylvinyl ether, hept-3-yn-1-ol, by a double decomposition reaction of its tosylate with lithium bromide.The key synthon - dodec-8-yn-1-ol - was converted with the aid of sodium in liquid ammonia into the stereochemical individual dodec-8E-enol, while its reduction with the aid of 9-borabicyclononane (BBN) gave the stereoisomeric alcohol exclusively with the Z configuration, as followed from the results of capillary GLC and the IR spectra of the corresponding acetates.The PMR spectra of the compounds synthesized are also given.
- Odinokov, V. N.,Ishmuratov, G. Yu.,Balezina, G. G.,Tolstikov, G. A.
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p. 372 - 374
(2007/10/02)
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