Literature DB >> 19802347

Enantio- and Diastereodivergent Synthetic Route to Multifarious Cyclitols from D-Xylose via Ring-Closing Metathesis.

Giovanni Luchetti1, Kejia Ding, Marc d'Alarcao, Alexander Kornienko.   

Abstract

Short stereoselective syntheses of various cyclitols, including the derivatives of conduritol B, conduritol F, myo-inositol and chiro-inositol, have been accomplished. The key steps in the syntheses are a ring-closing metathesis process and a diastereodivergent organometallic addition to a D-xylose-derived alde-hyde.

Entities:  

Year:  2008        PMID： 19802347      PMCID： PMC2711561          DOI： 10.1055/s-2008-1067260

Source DB:  PubMed          Journal:  Synthesis (Stuttg)        ISSN： 0039-7881            Impact factor:   3.157


  19 in total

1.  Synthesis of cycloheptenols from carbohydrates by ring-closing metathesis

Authors: 
Journal:  J Org Chem       Date:  2000-08-25       Impact factor: 4.354

2.  Regioselective protection and deprotection of inositol hydroxyl groups.

Authors:  Kana M Sureshan; Mysore S Shashidhar; Thoniyot Praveen; Tanya Das
Journal:  Chem Rev       Date:  2003-11       Impact factor: 60.622

3.  Production, isolation and structure determination of a novel beta-glucosidase inhibitor, cyclophellitol, from Phellinus sp.

Authors:  S Atsumi; K Umezawa; H Iinuma; H Naganawa; H Nakamura; Y Iitaka; T Takeuchi
Journal:  J Antibiot (Tokyo)       Date:  1990-01       Impact factor: 2.649

4.  Biochemical studies on 2-deoxy-scyllo-inosose, an early intermediate in the biosynthesis of 2-deoxystreptamine. I. Chemical synthesis of 2-deoxy-scyllo-inosose and [2,2-2H2]-2-deoxy-scyllo-inosose.

Authors:  N Yamauchi; K Kakinuma
Journal:  J Antibiot (Tokyo)       Date:  1992-05       Impact factor: 2.649

5.  Enantiodivergent formal synthesis of (+)- and (-)-cyclophellitol from D-xylose based on the latent symmetry concept.

Authors:  Artem S Kireev; August T Breithaupt; William Collins; Oleg N Nadein; Alexander Kornienko
Journal:  J Org Chem       Date:  2005-01-21       Impact factor: 4.354

6.  Active site-directed inhibition of galactosidases by conduritol C epoxides (1,2-anhydro-epi- and neo-inositol).

Authors:  G Legler; M Herrchen
Journal:  FEBS Lett       Date:  1981-11-30       Impact factor: 4.124

7.  Synthesis of enantiomerically pure, highly functionalized, medium-sized carbocycles from carbohydrates: formal total synthesis of (+)-calystegine b(2).

Authors:  José Marco-Contelles; Elsa de Opazo
Journal:  J Org Chem       Date:  2002-05-31       Impact factor: 4.354

8.  Asymmetric induction in methyl ketone aldol additions to alpha-alkoxy and alpha,beta-bisalkoxy aldehydes: a model for acyclic stereocontrol.

Authors:  David A Evans; Victor J Cee; Sarah J Siska
Journal:  J Am Chem Soc       Date:  2006-07-26       Impact factor: 15.419

9.  Biological activities of cyclophellitol.

Authors:  S Atsumi; H Iinuma; C Nosaka; K Umezawa
Journal:  J Antibiot (Tokyo)       Date:  1990-12       Impact factor: 2.649

10.  Synthesis of anti-tumour phosphatidylinositol analogues from glucose by the use of ring-closing olefin metathesis.

Authors:  Thomas L Andresen; Dorthe M Skytte; Robert Madsen
Journal:  Org Biomol Chem       Date:  2004-09-16       Impact factor: 3.876
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  2 in total

Review 1.  The "Other" Inositols and Their Phosphates: Synthesis, Biology, and Medicine (with Recent Advances in myo-Inositol Chemistry).

Authors:  Mark P Thomas; Stephen J Mills; Barry V L Potter
Journal:  Angew Chem Int Ed Engl       Date:  2015-12-22       Impact factor: 15.336

2.  The myo-1,2-Diaminocyclitol Scaffold Defines Potent Glucocerebrosidase Activators and Promising Pharmacological Chaperones for Gaucher Disease.

Authors:  Ana Trapero; Amadeu Llebaria
Journal:  ACS Med Chem Lett       Date:  2011-05-18       Impact factor: 4.345
  2 in total

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