69684-81-7Relevant academic research and scientific papers
Synthesis of (±)-β-Allokainic Acid
Piotrowski, Mathew L.,Kerr, Michael A.
, p. 3122 - 3126 (2019/06/08)
The total synthesis of kainoid alkaloid, (+/–)-β-allokainic acid is reported. The key step is a vinylogous Cloke–Wilson rearrangement followed by Lewis acid and transition metal induced transformations to prepare a highly functionalized pyrrolidine suitable for conversion to the target molecule.
Substrate stereocontrol in the intramolecular organocatalyzed tsuji-trost reaction: Enantioselective synthesis of allokainates
Vulovic, Bojan,Gruden-Pavlovic, Maja,Matovic, Radomir,Saicic, Radomir N.
supporting information, p. 34 - 37 (2014/01/23)
Organocatalyzed Tsuji-Trost cyclization of 3b proceeds with asymmetric induction and allows for stereoselective synthesis of (+)-allokainic acid. The stereochemical outcome of the cyclization was predicted by calculations.
Total synthesis of (±)-kainic acid: A photochemical C-H carbamoylation approach
Kamon, Takuma,Irifune, Yayoi,Tanaka, Tetsuaki,Yoshimitsu, Takehiko
supporting information; experimental part, p. 2674 - 2677 (2011/07/07)
A novel photochemical C-H carbamoylation of an octahydroisoindole derivative with PhNCO has allowed the authors to provide a unique access to a highly functionalized proline motif from which total synthesis of (±)-kainic acid, a bioactive marine alkaloid, has been accomplished.
Di- and trisubstituted γ-lactams via Rh(II)-carbenoid reaction of N -Cα-branched, N -Bis(trimethylsilyl)methyl α-diazoamides. Synthesis of (±)-α-allokainic acid
Zhang, Bao,Wee, Andrew G. H.
supporting information; experimental part, p. 5386 - 5389 (2011/03/17)
Acyclic N-Cα-branched, N-bis(trimethylsilyl)methyl (N-BTMSM) diazoamides undergo regio-, chemo-, and diastereoselective Rh(II)-carbenoid C-H insertion to give 4,5-disubstituted and 3,4,5-trisubstituted γ-lactams. The conformational influence of
Ruthenium-catalyzed cycloisomerizations of diynols
Trost, Barry M.,Rudd, Michael T.
, p. 4763 - 4776 (2007/10/03)
A wide variety of diynols containing tertiary, secondary, and primary propargylic alcohols undergo a cycloisomerization reaction to form dienones and dienals in the presence of a catalytic amount of [CpRu(CH3CN) 3]PF6. The
Stereocontrolled syntheses of kainoid amino acids from 7-azabicyclo[2.2.1] heptadienes using tandem radical addition-homoallylic radical rearrangement
Hodgson, David M.,Hachisu, Shuji,Andrews, Mark D.
, p. 8866 - 8876 (2007/10/03)
N-Boc syn-7-(2-hydroxyethyl)-4-(alkyl or aryl)sulfonyl-2-azabicyclo[2.2.1] hept-5-enes serve as precursors in syntheses of the neuroexcitants 3-(carboxymethyl)pyrrolidine-2,4-dicarboxylic acid 43, α-kainic acid 12, α-isokainic acid 14, and α-dihydroalloka
Total synthesis of (+/-)-kainic Acid with an aza-[2,3]-Wittig sigmatropic rearrangement as the key stereochemical determining step.
Anderson, James C,Whiting, Matthew
, p. 6160 - 6163 (2007/10/03)
A flexible route to the kainoid skeleton is exemplified by the synthesis of (+/-)-kainic acid from 3-butyn-1-ol. The route relies on the aza-[2,3]-Wittig sigmatropic rearrangement to efficiently install the relative stereochemistry between C2-C3. The C4 s
Synthesis of (±)-kainic acid by dearomatising cyclisation of a lithiated N-benzyl p-anisamide
Clayden, Jonathan,Tchabanenko, Kirill
, p. 317 - 318 (2007/10/03)
N-Benzyl p-anisamide 6, on lithiation with Bu(t)Li in the presence of HMPA, undergoes a stereoselective anionic cyclisation with loss of aromaticity to give a bicyclic enone which may be converted in nine steps to (±)-kainic acid.
Stereoselective synthesis of (±)-α-kainic acid using free radical key reactions
Bachi, Mario D.,Bar-Ner, Nira,Melman, Artem
, p. 7116 - 7124 (2007/10/03)
Thiol-mediated free radical isomerization of a deliberately substituted but-3-enyl isocyanide 12a, and n-Bu3SnH/AIBN-mediated free radical cyclization of a deliberately substituted but-3-enyl isothiocyanate 22, afforded, respectively, the (ethylthio)pyrroline 13a and the thiopyroglutamates 5 and 23. Reduction, protection, and deprotection of these heterocyclic compounds afforded proline derivatives 6 and 25 which contain all the structural elements of α-kainic acid (1) except the C-2 acetic acid moiety. These intermediates were stereospecifically converted into (±)-α-kainic acid using a new method of temporary sulfur connection. Accordingly, CH2CO2Me is linked to the chiral isopropenyl anchor and then intramolecularly connected to the pyrrolidine ring and eventually disconnected from its anchor by a sequential reductive double elimination process in which the isopropenyl double bond is restored.
A Concise, Stereocontrolled Thiazolium Ylide Approach to Kainic Acid
Monn, James A.,Valli, Matthew J.
, p. 2773 - 2778 (2007/10/02)
Racemic α-kainic acid (1) has been prepared from (1SR,2SR,5RS)-ethyl (N-(benzyloxycarbonyl)-3-aza-6-oxobicyclooctane-2-carboxylate (11) in ca. 16percent overall yield via a concise six-step synthetic sequence.Compound 11 is prepared on a large scale in 50percent yield via the cycloaddition of thiazolium ylide 9 and 2-cyclopentenone, which provides the requisite 2,3-trans, 3,4-cis stereochemical array about the trisubstituted pyrrolidine nucleus in 1.Chemoselective addition of the one-to-one adduct of MeLi and TiCl4 to the ketone functionality in 11 followed by dehydration, oxidative ring opening, and nonbasis methylenation of the stereochemically labile C4 acetate moiety with CH2I2-Zn-TiCl4 affords the fully protected penultimate intermediate 17 which is exhaustively hydrolyzed to provide 1.This represents a highly efficient and stereocontrolled preparation of (+/-)-α-kainic acid.
