Literature DB >> 21113401

Versatile methodology for the synthesis and α-functionalization of (2R,3aS,7aS)-octahydroindole-2-carboxylic acid.

Francisco J Sayago1, M Isabel Calaza, Ana I Jiménez, Carlos Cativiela.   

Abstract

An improved strategy for the effective synthesis of enantiomerically pure (2R,3aS,7aS)-octahydroindole-2-carboxylic acid (Oic), based on the formation of a trichloromethyloxazolidinone derivative, has been developed. Additionally, the completely diastereoselective α-alkylation of such oxazolidinone provides a very convenient and concise route to enantiopure α-tetrasubstituted derivatives of this Oic stereoisomer.

Entities:  

Year:  2008        PMID： 21113401      PMCID： PMC2991158          DOI： 10.1016/j.tet.2007.10.095

Source DB:  PubMed          Journal:  Tetrahedron        ISSN： 0040-4020            Impact factor:   2.457


  18 in total

Review 1.  Control of peptide conformation by the Thorpe-Ingold effect (C alpha-tetrasubstitution).

Authors:  C Toniolo; M Crisma; F Formaggio; C Peggion
Journal:  Biopolymers       Date:  2001       Impact factor: 2.505

Review 2.  Development of conformationally restricted analogues of bradykinin and somatostatin using constrained amino acids and different types of cyclization.

Authors:  Siegmund Reissmann; Diana Imhof
Journal:  Curr Med Chem       Date:  2004-11       Impact factor: 4.530

Review 3.  Exploring Ramachandran and chi space: conformationally constrained amino acids and peptides in the design of bioactive polypeptide ligands.

Authors:  S M Cowell; Y S Lee; J P Cain; V J Hruby
Journal:  Curr Med Chem       Date:  2004-11       Impact factor: 4.530

4.  Design of peptides, proteins, and peptidomimetics in chi space.

Authors:  V J Hruby; G Li; C Haskell-Luevano; M Shenderovich
Journal:  Biopolymers       Date:  1997       Impact factor: 2.505

5.  Dysinosin A: a novel inhibitor of Factor VIIa and thrombin from a new genus and species of Australian sponge of the family Dysideidae.

Authors:  Anthony R Carroll; Gregory K Pierens; Greg Fechner; Priscila De Almeida Leone; Anna Ngo; Moana Simpson; Edward Hyde; John N A Hooper; Stig-Lennart Boström; Djordje Musil; Ronald J Quinn
Journal:  J Am Chem Soc       Date:  2002-11-13       Impact factor: 15.419

6.  Conformations of proline.

Authors:  D F De Tar; N P Luthra
Journal:  J Am Chem Soc       Date:  1977-02-16       Impact factor: 15.419

7.  Synthesis and structure-activity relationships of potent new angiotensin converting enzyme inhibitors containing saturated bicyclic amino acids.

Authors:  C J Blankley; J S Kaltenbronn; D E DeJohn; A Werner; L R Bennett; G Bobowski; U Krolls; D R Johnson; W M Pearlman; M L Hoefle
Journal:  J Med Chem       Date:  1987-06       Impact factor: 7.446

Review 8.  Perindopril: an updated review of its use in hypertension.

Authors:  M Hurst; B Jarvis
Journal:  Drugs       Date:  2001       Impact factor: 9.546

9.  The N-acyloxyiminium ion aza-Prins route to octahydroindoles: total synthesis and structural confirmation of the antithrombotic marine natural product oscillarin.

Authors:  Stephen Hanessian; Martin Tremblay; Jens F W Petersen
Journal:  J Am Chem Soc       Date:  2004-05-19       Impact factor: 15.419

10.  Synthesis and ACE inhibitory activity of the stereoisomers of perindopril (S 9490) and perindoprilate (S 9780).

Authors:  M Vincent; B Marchand; G Rémond; S Jaguelin-Guinamant; G Damien; B Portevin; J Y Baumal; J P Volland; J P Bouchet; P H Lambert
Journal:  Drug Des Discov       Date:  1992
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  4 in total

1.  A straightforward route to enantiopure alpha-substituted derivatives of (2S,3aS,7aS)-octahydroindole-2-carboxylic acid.

Authors:  Francisco J Sayago; M Isabel Calaza; Ana I Jiménez; Carlos Cativiela
Journal:  Tetrahedron       Date:  2009-07-01       Impact factor: 2.457

2.  Recent Progress on the Stereoselective Synthesis of Cyclic Quaternary alpha-Amino Acids.

Authors:  Carlos Cativiela; Mario Ordóñez
Journal:  Tetrahedron Asymmetry       Date:  2009-01-30

3.  Towards the stereoselective synthesis of alpha-methylated (2S,3aS,7aS)-octahydroindole-2-carboxylic acid.

Authors:  Francisco J Sayago; M Isabel Calaza; Ana I Jiménez; Carlos Cativiela
Journal:  Tetrahedron Asymmetry       Date:  2008-12-12

4.  Efficient access to enantiomerically pure cyclic alpha-amino esters through a lipase-catalyzed kinetic resolution.

Authors:  Sergio Alatorre-Santamaría; María Rodriguez-Mata; Vicente Gotor-Fernández; Marcos Carlos de Mattos; Francisco J Sayago; Ana I Jiménez; Carlos Cativiela; Vicente Gotor
Journal:  Tetrahedron Asymmetry       Date:  2009-01-25
  4 in total

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