Literature DB >> 20090865

Synthesis of Boc-protected bicycloproline.

Sujeewa Ranatunga1, Juan R Del Valle.   

Abstract

The synthesis of a highly constrained quaternary carbocyclic α-amino acid, (+)-N-Boc-bicycloproline, has been achieved starting from sodium cyclopentadienylide. Key steps include a rhodium-catalyzed nitrenoid C-H insertion to install the tert-alkylamine and a ring-closing metathesis reaction to form the pyrrolidine ring.

Entities:  

Year:  2009        PMID： 20090865      PMCID： PMC2808134          DOI： 10.1016/j.tetlet.2009.03.092

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  22 in total

Review 1.  Design of folded peptides.

Authors:  J Venkatraman; S C Shankaramma; P Balaram
Journal:  Chem Rev       Date:  2001-10       Impact factor: 60.622

2.  Design in topographical space of peptide and peptidomimetic ligands that affect behavior. A chemist's glimpse at the mind--body problem.

Authors:  V J Hruby
Journal:  Acc Chem Res       Date:  2001-05       Impact factor: 22.384

Review 3.  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

4.  A silver-catalyzed intramolecular amidation of saturated C--h bonds.

Authors:  Yong Cui; Chuan He
Journal:  Angew Chem Int Ed Engl       Date:  2004-08-13       Impact factor: 15.336

5.  Recent advances in catalytic intramolecular C-H aminations.

Authors:  Huw M L Davies; Matthew S Long
Journal:  Angew Chem Int Ed Engl       Date:  2005-06-06       Impact factor: 15.336

6.  Synthesis of 2-Azatricyclo[5.2.1.0(4,10)]decanes and 2,5-Diazatricyclo[5.2.1.0(4,10)]decanes by Intramolecular Azomethine Ylide Cycloadditions.

Authors:  Larry E. Overman; John E. Tellew
Journal:  J Org Chem       Date:  1996-11-15       Impact factor: 4.354

7.  Stereoselective synthesis of 3-substituted 2-aminocyclopentanecarboxylic acid derivatives and their incorporation into short 12-helical beta-peptides that fold in water.

Authors:  Matthew G Woll; John D Fisk; Paul R LePlae; Samuel H Gellman
Journal:  J Am Chem Soc       Date:  2002-10-23       Impact factor: 15.419

8.  Reductive cyclization of delta-hydroxy nitriles: a new synthesis of glycosylamines.

Authors:  Andrew D Dorsey; Jennifer E Barbarow; Dirk Trauner
Journal:  Org Lett       Date:  2003-09-04       Impact factor: 6.005

9.  Rearrangement of pyrrolines derived from the Birch reduction of electron-deficient pyrroles: radical ring-expansion to substituted tetrahydropyridines.

Authors:  Peter G Turner; Timothy J Donohoe; Rick P C Cousins
Journal:  Chem Commun (Camb)       Date:  2004-05-18       Impact factor: 6.222

10.  Controls exerted by the Aib residue: helix formation and helix reversal.

Authors:  I L Karle
Journal:  Biopolymers       Date:  2001       Impact factor: 2.505
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  1 in total

1.  Enantioselective synthesis of angularly substituted 1-azabicylic rings: coupled dynamic kinetic epimerization and chirality transfer.

Authors:  Zachary D Aron; Tatsuya Ito; Tricia L May; Larry E Overman; Jocelyn Wang
Journal:  J Org Chem       Date:  2013-09-10       Impact factor: 4.354
  1 in total

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