- Diastereoselective synthesis of functionalised carbazoles via a sequential Diels-Alder/ene reaction strategy
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An operationally simple one-pot, three-component, diastereoselective synthesis of saturated carbazoles and related pyridazino[3,4-b]indoles, based on two sequential intermolecular pericyclic reactions, is described. The reaction sequence involves an intermolecular Diels-Alder (D-A) reaction of a 3-vinyl-1H-indole, containing an electron withdrawing N-protecting group, with a suitable dienophile. Due to the electron withdrawing nature of the N-protecting group the resultant D-A cycloadducts are sufficiently stabilised to allow for a subsequent in situ diastereospecific intermolecular ene reaction to take place with an added enophile, generating functionalised carbazoles with relative stereocontrol of up to four stereocentres.
- Cowell, Joseph,Abualnaja, Matokah,Morton, Stephanie,Linder, Ruth,Buckingham, Faye,Waddell, Paul G.,Probert, Michael R.,Hall, Michael J.
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p. 16125 - 16152
(2015/03/04)
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- INDOLE-3-CARBINOL DERIVATIVES
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The present invention relates to novel stable indole-3-carbinol derivatives of Formula-I and its pharmaceutical composition and biological activity. The present invention includes compositions and methods for the treatment and prevention of conditions ass
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Page/Page column 17
(2015/02/02)
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- Unusual reactivity of nitronates with an aryl alkyl carbonate: Synthesis of α-amino esters
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The monoanions of nitroalkanes are ambident nucleophiles that react with carbonate electrophiles through the oxygen atom. Products arising from reactivity at the carbon atom will yield α-nitro esters, which are precursors for α-amino esters. We demonstrate this in the reactions of nitroalkanes with benzyl phenyl carbonate and DABCO where α-nitro esters are obtained instead of nitrile oxides. The products are readily reduced to α-amino esters. This pathway could be a safe alternative to the Strecker reaction.
- Reddy, Golipalli Ramana,Mukherjee, Debopreeti,Chittoory, Arjun Kumar,Rajaram, Sridhar
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supporting information
p. 5874 - 5877
(2015/01/08)
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- A new synthetic method for the preparation of α,β-didehydroamino acid derivatives by means of a wittig-type reaction. Syntheses of (2S, 4S)- and (2R, 4R)-4-hydroxyprolines
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Ethyl N-Boc- and N-Z-α-tosylglycinates were reacted with a variety of aldehydes in the presence of tributylphosphine and a base to afford the corresponding α,β-didehydroamino acid derivatives with high (Z)-selectivity in good yields. Moreover, ethyl (4S)- and (4R)-2-(N-Boc-amino)-4,5-isopropylidenedioxy-2-pentenoates prepared by the present method were converted to (2S, 4S)- and (2R, 4R)-4-hydroxyprolines, respectively.
- Kimura, Rumi,Nagano, Tanemasa,Kinoshita, Hideki
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p. 2517 - 2525
(2007/10/03)
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- Structure-activity dependency of new bacterial tryptophanyl tRNA synthetase inhibitors
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Analogues of the aminoacyl tRNA synthetase inhibitor, indolmycin, have been synthesised in which the side chain methyl group is replaced by a wide range of substituents. Their antibacterial and enzyme inhibitory potency is related to steric properties and
- Witty, David R.,Walker, Graham,Bateson, John H.,O'Hanlon, Peter J.,Cassels, Robert
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p. 1375 - 1380
(2007/10/03)
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- Antibacterial 2-amino-oxazolinones and process therefor
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A series of novel antibacterially active derivatives of indolmycin as well as some prodrug forms of indolmycin is disclosed. A novel process for the production of these compounds is also disclosed.
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- New Total Synthesis of (+/-)-Indolmycin
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A convergent total synthesis of the antibiotic (+/-)-indolmycin (1) is presented.N-Carbobenzoxy-3-(1-chloroethyl)indole (12) is prepared in three steps from indole-3-carboxaldehyde (9).Alkylation of the lithium anion of 2-(dimethylamino)-4(5H)-oxazolone (4) with chloride (12) provides a mixture of the (+/-)-2-dimethylamino derivative of indolmycin (13) and its diastereomer (14) in a ratio of 2.2:1.Amine exchange is effected by treatment of 13 with methylamine, affording (+/-)-1 in five steps from commercially available 9.Efforts to extend this technology toward an asymmetric synthesis of (-)-1 are described.
- Dirlam, John P.,Clark, David A.,Hecker, Scott J.
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p. 4920 - 4924
(2007/10/02)
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- DIOXOLANE ANALOGS OF C-NUCLEOSIDES OF INDOLE AND A SUBSTITUTED 9-DEAZAPURINE
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Cyclic acetals of N-acyl derivatives of 3-formylindole and 3-formyl-5-phenyl-7-ethylthiopyrrolopyrimidine, which may be viewed as analogs of the α and β anomers of C-nucleosides modified in the carbohydrate part of the molecule, have been obtained.
- Shingarova, I. D.,Sizova, O. S.,Preobrazhenskaya, M. N.
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p. 1188 - 1191
(2007/10/02)
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- ASYMMETRIC TOTAL SYNTHESIS OF INDOLMYCIN
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An asymmetric total synthesis of indolmycin was achieved via a key intermediate, α-indolmycenic acid ester.The ester was obtained by oxygenation of methyl (S)-3-(3-indolyl)butanoate which was prepared by asymmetric synthesis utilizing (2R,3S)-3,4-dimethyl
- Takeda, Takeshi,Mukaiyama, Teruaki
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p. 163 - 166
(2007/10/02)
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