80226-74-0Relevant articles and documents
Practical synthesis of (-)-1-amino-1-deoxy-myo-inositol from achiral precursors
Gonzalez-Bulnes, Patricia,Casas, Josefina,Delgado, Antonio,Llebaria, Amadeu
, p. 1947 - 1952 (2008/02/10)
A new synthesis of enantiomerically pure 1-amino-1-deoxy-myo-inositol is reported. The route described employs p-benzoquinone, an achiral compound, as the starting material to give conduritol B tetraacetate in three steps. Kinetic resolution of this compound using a palladium catalyst with a chiral ligand allows access to a conduritol B tetraester in high enantiomeric excess. This compound is transformed into tetrabenzyl conduritol B epoxide, which is regioselectively opened with azide to give the key azidocyclitol. Final transformation into (-)-1-amino-1-deoxy-myo-inositol hydrochloride is achieved in four synthetic steps. This sequence allows the synthesis of this compound in high enantiomeric purity in a semi-preparative scale.
Synthesis of both enantiomers of conduritol C tetraacetate and of meso-conduritol D tetraacetate by oxidation of benzoquinone bis(ethylene acetal)
Lang, Martin,Ziegler, Thomas
, p. 768 - 776 (2008/02/07)
Epoxidation of p-benzoquinone bis(ethylene acetal) (1) with m-chloroperbenzoic acid or hydrogen peroxide/benzonitrile afforded corresponding monoepoxide 2, which was converted into p-benzoquinone mono(ethylene acetal) monoepoxide 5 with perchloric acid. D
Synthesis of haloconduritols from an endo-cycloadduct of furan and vinylene carbonate
Baran, Arif,Kazaz, Cavit,Se?en, Hasan,Sütbeyaz, Ya?ar
, p. 3643 - 3648 (2007/10/03)
A method for preparing haloconduritols having a conduritol-A construction is described. A mixture of endo- and exo-cycloadduct derivatives prepared from the Diels-Alder reaction of furan and vinylene carbonate was converted into diacetate derivatives by hydrolysis (K2CO3/MeOH) followed by acetylation (Ac2O/pyridine). Boron trihalide (BBr3 or BCl3)-assisted ring-opening of the endo-diacetate in CH2Cl2 at -78°C gave (1α,2α,3β,6β)-6-halogeno-4-cyclohexene-1,2,3-triol 1,2-diacetate from which the corresponding triacetate was prepared by acetylation (AcCl). trans-Esterification of the triacetate (MeOH/HCl) afforded (1α,2α,3β,6β)-6-halogeno-4-cyclohexene-1,2,3-triol (X=Br or Cl). BF3-Assisted ring-opening of the endo-diacetate in CH2Cl2 gave (1α,2α,3β,6β)-6-chloro-4-cyclohexene-1,2,3-triol 1,2-diacetate by means of halogen exchange.
Stereoselective synthesis of myo-, neo-, L-chiro, D-chiro, allo-, scyllo-, and epi-inositol systems via conduritols prepared from p-benzoquinone
Podeschwa, Michael,Plettenburg, Oliver,Vom Brocke, Jochen,Block, Oliver,Adelt, Stephan,Altenbach, Hans-Josef
, p. 1958 - 1972 (2007/10/03)
A practical route is described for the flexible preparation of a wide variety of inositol stereoisomers and their polyphosphates. The potential of this approach is demonstrated by the synthesis of myo-, L-chiro-, D-chiro-, epi-, scyllo-, allo-, and neo-inositol systems. Optically pure compounds in either enantiomeric form can be prepared from p-benzoquinone via enzymatic resolution of a derived conduritol B key intermediate. High-performance anion-exchange chromatography with pulsed amperometric detection permits inositol stereoisomers to be resolved and detected with high sensitivity. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.
Asymmetric induction of conduritols via AAA reactions: Synthesis of the aminocyclohexitol of hygromycin A
Trost, Barry M.
, p. 1619 - 1629 (2007/10/03)
Two synthetic routes towards the construction of the aminocyclohexitol moiety of hygromycin A have been developed based on palladium-catalyzed asymmetric alkylation of conduritol derivatives. A protocol has been established whereby this biologically relev
From cycloolefins to chiral, polyfunctionalized linear C6/C12 building blocks - Biocatalysis, (-)-conduramine E
Spielvogel,Kammerer,Keller,Prinzbach
, p. 7863 - 7867 (2007/10/03)
1,4-Cyclohexadiene is the starting material for the expeditious synthesis of the 1S2S3S4R- and 1R2R3R4S-epoxy-cyclohexene-1,4-diol monoacetates through enzyme-catalyzed hydrolysis and transesterification, respectively. The absolute configurations are established by correlation of (-)-10 and known (+)-conduramine E. Ozonation and functional group manipulation open access to fully protected, polyfunctionalized C6-aldehydes whose reductive coupling to C2-symmetrical C12 building blocks is being explored. (C) 2000 Elsevier Science Ltd.
Carbohydrate carbocyclization by a novel zinc-mediated domino reaction and ring-closing olefin metathesis
Hyldtoft, Lene,Madsen, Robert
, p. 8444 - 8452 (2007/10/03)
A general method for carbocyclization of carbohydrates is described using two consecutive organometallic transformations: a novel zinc-mediated domino reaction to give functionalized dienes followed by ring-closing olefin metathesis. In the first reaction
Pd catalyzed kinetic resolution of conduritol B. Asymmetric synthesis of (+)-cyclophellitol
Trost,Hembre
, p. 219 - 222 (2007/10/03)
Enantiomerically pure (+)-cyclophellitol is readily available from benzoquinone employing an asymmetric palladium catalyzed kinetic resolution of racemic conduritol B and a novel easily cleavable pivalate analogue.
An efficient enzymatic preparation of (+)- and (-)-conduritol E, a cyclitol with C2 symmetry
Sanfilippo, Claudia,Patti, Angela,Piattelli, Mario,Nicolosi, Giovanni
, p. 1569 - 1573 (2007/10/03)
Lypozyme IM (immobilised lipase from Mucor miehei) catalyses the enantiomeric alcoholysis of tetraacetylconduritol E (±)-2 to give enantiopure (1R,2R,3R,4R)-tetrahydroxycyclohex-5-ene (-)-1, and the unreacted ester (1S,2S,3S,4S)-tetraacetyloxycyclohex-5-ene, (+)-2. The latter was transformed by basic hydrolysis into (+)-1 in high yield and 95% ee. Selective amination of partial ester (-)-3, obtained by short alcoholysis of (±)-2, furnished the previously unreported conduramine F-4, (-)-4.
Stereochemical observations on the bromate induced monobromopentahydroxylation of benzene by catalytic photoinduced charge transfer osmylation. A concise synthesis of (±)-pinitol
Jung, Pierre M. J.,Motherwell, William B.,Williams, Alvin S.
, p. 1283 - 1284 (2007/10/03)
The use of lower temperatures in the title reaction favours the formation of the neo diastereoisomer of the deoxybromoinositol whose diisopropylidene derivative can be converted in three steps to (±)-pinitol.
