Organic Letters (ORG LETT)

Publications in this journal

• Article: Eight Stereoisomers of Homonojirimycin from D-Mannose

  Gabriel M. J. Lenagh-Snow, Sarah F. Jenkinson, Scott J. Newberry, Atsushi Kato, Shinpei Nakagawa, Isao Adachi, Mark R. Wormald, Akihide Yoshihara, Kenji Morimoto, Kazuya Akimitsu, Ken Izumori, George W. J. Fleet
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  ABSTRACT: Although there are 32 6-azidoheptitols, there are only 16 homonojirimycin (HNJ) stereoisomers. Two epimeric azidoalditols derived from d-mannose allow the synthesis in water of eight stereoisomers of HNJ.
  Organic Letters 04/2012; 14(8):2050-2053.
• Article: Azetidine Iminosugars from the Cyclization of 3,5-Di-O-triflates of α-Furanosides and of 2,4-Di-O-triflates of β-Pyranosides Derived from Glucose

  Gabriel M. J. Lenagh-Snow, Noelia Araújo, Sarah F. Jenkinson, R. Fernando Martínez, Yousuke Shimada, Chu-Yi Yu, Atsushi Kato, George W. J. Fleet
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  ABSTRACT: Primary amines with either 3,5-di-O-ditriflates of α-furanosides or 2,4-di-O-triflates of β-pyranosides form bicyclic azetidines in high yield.
  Organic Letters 04/2012; 14(8):2142–2145.
• Article: Ruthenium Catalyzed Synthesis of Enaminones

  Naga Durgarao Koduri, Halee Scott, Bethany Hileman, Justin D. Cox, Michael Coffin, Lindsay Glicksberg, and Syed R. Hussaini
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  ABSTRACT: The Grubbs first-generation catalyst has been found to be an effective catalyst for the synthesis of enaminones by coupling thioamides with R-diazodicarbonyl compounds. The reaction is successful in converting primary, secondary, and tertiary thioamides into their corresponding enaminones. The reaction is also suitable for the synthesis of chiral enaminones.
  Organic Letters 01/2012; 14(2):440-443.
• Article: Tandem Rh(III)-Catalyzed Oxidative Acylation of Secondary Benzamides with Aldehydes and Intramolecular Cyclization: The Direct Synthesis of 3-Hydroxy-isoindolin-1-ones

  Satyasheel Sharma, Eonjeong Park, Jihye Park, In Su Kim
  Organic Letters 01/2012;
• Article: Inhibition of nonmammalian glycosidases by azetidine iminosugars derived from stable 3,5-di-O-triflates of pentoses

  Gabriel M. J. Lenagh-Snow, Noelia Araujo, Sarah F. Jenkinson, Catherine Rutherford, Shinpei Nakagawa, Atsushi Kato, Chu-Yi Yu, Alexander C. Weymouth-Wilson, George W. J. Fleet
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  ABSTRACT: Efficient ring closure of stable crystalline 3,5-di-O-triflates of pentofuranosides with amines to form azetidines allowed preliminary evaluation of four-ring iminosugars as glycosidase inhibitors; significant and specific inhibition of nonmammalian α-glucosidases is shown by l-xylo- and l-arabino-iminosugar azetidines.
  Organic Letters 10/2011; 13(21):5834–5837.
• Article: Synthesis of fully substituted polyhydroxylated pyrrolizidines via Cope-House cyclization

  Wei Zhang, Kasumi Sato, Atsushi Kato, Yue-Mei Jia, Xiang-Guo Hu, Francis X. Wilson, Renate van Well, Graeme Horne, George W. J. Fleet, Robert J. Nash, Chu-Yi Yu
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  ABSTRACT: Total synthesis of the proposed structure of (−)-hyacinthacine C5 and its epimers at C6 and C7 is described. A key step of the synthesis was the construction of the bicyclic pyrrolizidine system by means of a nucleophilic addition of a dithiane to a cyclic nitrone followed by a Cope–House cyclization.
  Organic Letters 07/2011; 13(16):4414–4417.
• Article: Looking-glass synergistic pharmacological chaperones: DGJ and L-DGJ from the enantiomers of tagatose

  Sarah F. Jenkinson, George W. J. Fleet, Robert J. Nash, Yuriko Koike, Isao Adachi, Akihide Yoshihara, Kenji Morimoto, Ken Izumori, Atsushi Kato
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  ABSTRACT: The enantiomers of tagatose are converted to L-DGJ [a noncompetitive inhibitor of human lysosome α-galactosidase A (α-Gal A), Ki 38.5 μM] and DGJ [a competitive inhibitor of α-Gal A, Ki 15.1 nM] in 66% yield. L-DGJ and DGJ provide the first examples of pharmacological chaperones that (a) are enantiomeric iminosugars and (b) have synergistic activity with implications for the treatment of lysosomal storage disorders and other protein deficiencies.
  Organic Letters 07/2011; 13(15):4064–4067.
• Article: Synthesis of beta,gamma-Dihydroxyhomotyrosines by a Tandem Petasis-Asymmetric Dihydroxylation Approach

  Quentin I Churches, Jonathan M White, Craig A Hutton
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  ABSTRACT: Petasis reactions of substituted styrenylboronic acids and glyoxylic acid, employing tert-butylsulfinamide as the `amine' component, proceed with high stereoselectivity to produce beta,gamma-dehydrohomoarylalanine derivatives. Subsequent asymmetric dihydroxylation under neutral conditions gives the corresponding protected beta,gamma-dihydroxyhomoarylalanines with up to 15:1 dr. The method has been exploited in the efficient, stereoselective synthesis of protected beta,gamma-dihydroxyhomotyrosine, a component of the antifungal cyclic peptide echinocandin B.
  Organic Letters 01/2011; 13(11):2900-2903.
• Article: Synthesis and Glycosidase Inhibition of the Enantiomer of (−)-Steviamine, the First Example of a New Class of Indolizidine Alkaloid

  Xiang-Guo Hu, Barbara Bartholomew, Robert J. Nash, Francis X. Wilson, George W. J. Fleet, Shinpei Nakagawa, Atsushi Kato, Yue-Mei Jia, Renate van Well, Chu-Yi Yu
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  ABSTRACT: (+)-Steviamine, the enantiomer of the natural (−)-steviamine, and its corresponding C5 epimer have been synthesized from the d-ribose-derived cyclic nitrone. (−)-Steviamine was found to be the first naturally occurring iminosugar that causes any inhibition of α-galactosaminidases.
  Organic Letters 05/2010; 12(11):2562–2565.
• Article: Selective synthesis of eight-membered cyclic ureas by the [6 + 2] cycloaddition reaction of 2-vinylazetidines and electron-deficient isocyanates. [Erratum to document cited in CA152:037560].

  Shunsuke Koya, Kenichi Yamanoi, Ryu Yamasaki, Isao Azumaya, Hyuma Masu, Shinichi. Saito
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  ABSTRACT: On page 5438, in the bottom right column, in ref 3, ref. f was omitted, and should read: (f) Alcaide, B.; Almendros, P.; Aragoncillo, C. Chem. Rev. 2007, 107, 4437-4492.. [on SciFinder(R)]
  Organic Letters 01/2010; 12(4):896.
• Article: Organocatalytic aziridine synthesis using F+ salts. [Erratum to document cited in CA151:448132].

  Sean P. Bew, Polly-Anna Ashford, Shirley A. Fairhurst, David L. Hughes, Laurent Legentil, John Liddle, Paolo Pesce, Sanket Nigudkar, Martin A. Wilson
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  ABSTRACT: On page 4552, the following name and affiliation, was omitted from the author list, Polly-Anna Ashford, University of East Anglia. The correct version of the author list is given. [on SciFinder(R)]
  Organic Letters 01/2010; 12(10):2446.
• Article: Synthesis of Indene Derivatives via Electrophilic Cyclization.

  Zulfiqar Ali Khan, Thomas Wirth
  Organic Letters 01/2009;
• Article: Rh(I)-catalyzed reaction of 2-(chloromethyl)phenylboronic acids and alkynes leading to indenes.

  Masaki Miyamoto, Yasuyuki Harada, Mamoru Tobisu, Naoto Chatani
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  ABSTRACT: The reaction of 2-(chloromethyl)phenylboronic acid (1) with alkynes in the presence of a Rh(I) complex gave indene derivatives in high yields. The regioselectivity depends on the steric nature of the substituent on the alkynes. A bulky group favors the alpha-position of indenes.
  Organic Letters 08/2008; 10(14):2975-8.
• Article: Exploiting quadrupolar interactions in the synthesis of the macrocyclic portion of longithorone C.

  Joseph E Zakarian, Yassir El-Azizi, Shawn K Collins
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  ABSTRACT: 2,3,4,5,6-Pentafluorobenzyl and 3,5-bistrifluoromethylbenzyl ester auxiliaries can enable difficult macrocyclizations to afford rigid all-carbon paracyclophanes. The effectiveness of these auxiliaries has been demonstrated in preparing the carbon skeleton of the macrocyclic natural product longithorone C.
  Organic Letters 08/2008; 10(14):2927-30.
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  Article: Rhenium-catalyzed synthesis of multisubstituted aromatic compounds via C-C single-bond cleavage.

  Yoichiro Kuninobu, Hisatsugu Takata, Atsushi Kawata, Kazuhiko Takai
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  ABSTRACT: A reaction between a beta-keto ester and an acetylene in the presence of a rhenium complex, [ReBr(CO)3(thf)]2, as a catalyst, provided a 2-pyranone derivative in excellent yield via retro-aldol reaction (C-C single bond cleavage). By adding an acetylene-bearing ester group(s) after the formation of 2-pyranones, an aromatization reaction proceeded and multisubstituted aromatic compounds were obtained in good to excellent yields.
  Organic Letters 08/2008; 10(14):3133-5.