74639-50-2Relevant academic research and scientific papers
Diastereoselective synthesis of functionalised carbazoles via a sequential Diels-Alder/ene reaction strategy
Cowell, Joseph,Abualnaja, Matokah,Morton, Stephanie,Linder, Ruth,Buckingham, Faye,Waddell, Paul G.,Probert, Michael R.,Hall, Michael J.
, p. 16125 - 16152 (2015/03/04)
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.
INDOLE-3-CARBINOL DERIVATIVES
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Page/Page column 17, (2015/02/02)
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
Unusual reactivity of nitronates with an aryl alkyl carbonate: Synthesis of α-amino esters
Reddy, Golipalli Ramana,Mukherjee, Debopreeti,Chittoory, Arjun Kumar,Rajaram, Sridhar
supporting information, p. 5874 - 5877 (2015/01/08)
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.
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
Kimura, Rumi,Nagano, Tanemasa,Kinoshita, Hideki
, p. 2517 - 2525 (2007/10/03)
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.
Structure-activity dependency of new bacterial tryptophanyl tRNA synthetase inhibitors
Witty, David R.,Walker, Graham,Bateson, John H.,O'Hanlon, Peter J.,Cassels, Robert
, p. 1375 - 1380 (2007/10/03)
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
Antibacterial 2-amino-oxazolinones and process therefor
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, (2008/06/13)
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.
New Total Synthesis of (+/-)-Indolmycin
Dirlam, John P.,Clark, David A.,Hecker, Scott J.
, p. 4920 - 4924 (2007/10/02)
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.
DIOXOLANE ANALOGS OF C-NUCLEOSIDES OF INDOLE AND A SUBSTITUTED 9-DEAZAPURINE
Shingarova, I. D.,Sizova, O. S.,Preobrazhenskaya, M. N.
, p. 1188 - 1191 (2007/10/02)
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.
ASYMMETRIC TOTAL SYNTHESIS OF INDOLMYCIN
Takeda, Takeshi,Mukaiyama, Teruaki
, p. 163 - 166 (2007/10/02)
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
