Literature DB >> 20640170

Dimerization of (+)-Myrmicarin 215B. A Potential Biomimetic Approach to Complex Myrmicarin Alkaloids.

Alison E Ondrus1, Mohammad Movassaghi.   

Abstract

The acid promoted diastereoselective dimerization of myrmicarin 215B is described. The reactivity of these sensitive alkaloids, structural assignment, and a possible mechanism for the observed dimerization are discussed. These finding raise the intriguing possibility of the synthesis of the highly sensitive myrmicarin alkaloids based on a strategy involving the direct dimerization of functional tricyclic myrmicarin derivatives.

Entities:  

Year:  2006        PMID： 20640170      PMCID： PMC2904612          DOI： 10.1016/j.tet.2006.01.108

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


  10 in total

1.  Highly regioselective Vilsmeier-Haack acylation of hexahydropyrroloindolizine.

Authors:  B Sayah; N Pelloux-Léon; A Milet; J Pardillos-Guindet; Y Vallée
Journal:  J Org Chem       Date:  2001-04-06       Impact factor: 4.354

2.  First synthesis of nonracemic (R)-(+)-myrmicarin 217

Authors: 
Journal:  J Org Chem       Date:  2000-05-09       Impact factor: 4.354

3.  Palladium-catalyzed synthesis of N-vinyl pyrroles and indoles.

Authors:  Mohammad Movassaghi; Alison E Ondrus
Journal:  J Org Chem       Date:  2005-10-14       Impact factor: 4.354

4.  Palladium-catalyzed stereocontrolled vinylation of azoles and phenothiazine.

Authors:  Artyom Y Lebedev; Vyatcheslav V Izmer; Denis N Kazyul'kin; Irina P Beletskaya; Alexander Z Voskoboynikov
Journal:  Org Lett       Date:  2002-02-21       Impact factor: 6.005

5.  Enantioselective total synthesis of tricyclic myrmicarin alkaloids.

Authors:  Mohammad Movassaghi; Alison E Ondrus
Journal:  Org Lett       Date:  2005-09-29       Impact factor: 6.005

6.  Preparation of enamides via palladium-catalyzed amidation of enol tosylates.

Authors:  Artis Klapars; Kevin R Campos; Cheng-Yi Chen; Ralph P Volante
Journal:  Org Lett       Date:  2005-03-17       Impact factor: 6.005

7.  Catalytic enantioselective conjugate reduction of lactones and lactams.

Authors:  Gregory Hughes; Masanari Kimura; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2003-09-17       Impact factor: 15.419

8.  CuH-catalyzed asymmetric conjugate reductions of acyclic enones.

Authors:  Bruce H Lipshutz; Jeff M Servesko
Journal:  Angew Chem Int Ed Engl       Date:  2003-10-13       Impact factor: 15.336

9.  Copper-catalyzed asymmetric conjugate reduction as a route to novel beta-azaheterocyclic acid derivatives.

Authors:  Matthew P Rainka; Yimon Aye; Stephen L Buchwald
Journal:  Proc Natl Acad Sci U S A       Date:  2004-04-05       Impact factor: 11.205

10.  Palladium-catalyzed amidation of enol triflates: a new synthesis of enamides.

Authors:  Debra J Wallace; David J Klauber; Cheng-yi Chen; Ralph P Volante
Journal:  Org Lett       Date:  2003-11-27       Impact factor: 6.005
  10 in total
  4 in total

1.  Dimerization of functional pyrroloindolizines for the synthesis of complex myrmicarin alkaloids.

Authors:  Alison E Ondrus; H Ümit Kaniskan; Mohammad Movassaghi
Journal:  Tetrahedron       Date:  2010-06-26       Impact factor: 2.457

2.  Efficient and stereoselective dimerization of pyrroloindolizine derivatives inspired by a hypothesis for the biosynthesis of complex myrmicarin alkaloids.

Authors:  Mohammad Movassaghi; Alison E Ondrus; Bin Chen
Journal:  J Org Chem       Date:  2007-11-17       Impact factor: 4.354

3.  Total synthesis and study of myrmicarin alkaloids.

Authors:  Alison E Ondrus; Mohammad Movassaghi
Journal:  Chem Commun (Camb)       Date:  2009-05-19       Impact factor: 6.222

4.  Reversible dimerization of (+)-myrmicarin 215B.

Authors:  Alison E Ondrus; Mohammad Movassaghi
Journal:  Org Lett       Date:  2009-07-16       Impact factor: 6.005
  4 in total

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