Literature DB >> 22822275

Synthesis and Biological Evaluation of Cremastrine and an Unnatural Analogue.

Kristopher N Hahn1, Olugbeminiyi O Fadeyi, Hyekyung P Cho, Craig W Lindsley.   

Abstract

In this Letter, we describe the first total synthesis of cremastrine, a pyrrolizidine alkaloid from Cremastra appendiculata, with anticholinergic activity as well as an unnatural analogue. The streamlined synthesis proceeds in 9 steps, 7 steps longest linear sequence, in 25.2% overall yield, and features novel methodology to construct the pyrrolizidine core. Biological evaluation of cremastrine and the unnatural analogue indicated that both are pan-mAChR functional antagonists.

Entities:  

Year:  2012        PMID： 22822275      PMCID： PMC3398747          DOI： 10.1016/j.tetlet.2012.05.009

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


  14 in total

1.  Highly diastereoselective and general synthesis of primary β-fluoroamines.

Authors:  Michael L Schulte; Craig W Lindsley
Journal:  Org Lett       Date:  2011-09-26       Impact factor: 6.005

2.  Discovery and characterization of novel subtype-selective allosteric agonists for the investigation of M(1) receptor function in the central nervous system.

Authors:  Evan P Lebois; Thomas M Bridges; L Michelle Lewis; Eric S Dawson; Alexander S Kane; Zixiu Xiang; Satyawan B Jadhav; Huiyong Yin; J Phillip Kennedy; Jens Meiler; Colleen M Niswender; Carrie K Jones; P Jeffrey Conn; C David Weaver; Craig W Lindsley
Journal:  ACS Chem Neurosci       Date:  2010       Impact factor: 4.418

3.  A versatile enantioselective synthesis of azabicyclic ring systems: a concise total synthesis of (+)-grandisine D and unnatural analogues.

Authors:  Olugbeminiyi O Fadeyi; Timothy J Senter; Kristopher N Hahn; Craig W Lindsley
Journal:  Chemistry       Date:  2012-03-30       Impact factor: 5.236

4.  Cremastrine, a pyrrolizidine alkaloid from Cremastra appendiculata.

Authors:  Yoshitaka Ikeda; Hikaru Nonaka; Tamotsu Furumai; Yasuhiro Igarashi
Journal:  J Nat Prod       Date:  2005-04       Impact factor: 4.050

5.  Enantioselective transfer aminoallylation: synthesis of optically active homoallylic primary amines.

Authors:  Masaharu Sugiura; Chieko Mori; Shu Kobayashi
Journal:  J Am Chem Soc       Date:  2006-08-30       Impact factor: 15.419

6.  Ring expansion of azetidinium ylides: rapid access to the pyrrolizidine alkaloids turneforcidine and platynecine.

Authors:  John A Vanecko; F G West
Journal:  Org Lett       Date:  2005-07-07       Impact factor: 6.005

7.  A rapid and general method for the asymmetric synthesis of 2-substituted pyrrolidines using tert-butanesulfinamide.

Authors:  Kristin M Brinner; Jonathan A Ellman
Journal:  Org Biomol Chem       Date:  2005-05-04       Impact factor: 3.876

8.  Bistellettazines A-C and bistellettazole A: new terpenyl-pyrrolizidine and terpenyl-imidazole alkaloids from a southern Australian marine sponge, Stelletta sp.

Authors:  Mohamed El-Naggar; Andrew M Piggott; Robert J Capon
Journal:  Org Lett       Date:  2008-09-10       Impact factor: 6.005

Review 9.  Medicinal chemistry and therapeutic potential of muscarinic M3 antagonists.

Authors:  Ilaria Peretto; Paola Petrillo; Bruno P Imbimbo
Journal:  Med Res Rev       Date:  2009-11       Impact factor: 12.944

Review 10.  Subtype-selective allosteric modulators of muscarinic receptors for the treatment of CNS disorders.

Authors:  P Jeffrey Conn; Carrie K Jones; Craig W Lindsley
Journal:  Trends Pharmacol Sci       Date:  2009-02-07       Impact factor: 14.819
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  3 in total

1.  Towards the Total Synthesis of Marineosin A: Construction of the Macrocyclic Pyrrole and an Advanced, Functionalized Spiroaminal Model.

Authors:  Leslie N Aldrich; Cynthia B Berry; Brittney S Bates; Leah C Konkol; Miranda So; Craig W Lindsley
Journal:  European J Org Chem       Date:  2013-07-01

2.  Total synthesis of stemaphylline N-oxide and related C9a-epimeric analogues.

Authors:  Michael L Schulte; Mark L Turlington; Sharangdhar S Phatak; Joel M Harp; Shaun R Stauffer; Craig W Lindsley
Journal:  Chemistry       Date:  2013-08-16       Impact factor: 5.236

3.  A General, Enantioselective Synthesis of 1-Azabicyclo[m.n.0]alkane Ring Systems.

Authors:  Timothy J Senter; Michael L Schulte; Leah C Konkol; Tyler E Wadzinski; Craig W Lindsley
Journal:  Tetrahedron Lett       Date:  2013-03-27       Impact factor: 2.415
  3 in total

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