Literature DB >> 23311620

Synthesis of functionalized indolizidines through Pauson-Khand cycloaddition of 2-allylpyrrolidines.

Michael P McCormack1, Stephen P Waters.   

Abstract

A concise entry to functionalized indolizidine scaffolds through a domino 2-aza-Cope-[3 + 2] dipolar cycloaddition and Pauson-Khand [2 + 2 + 1] cyclization has been accomplished. The process was conducted under mild conditions to afford diverse indolizidine systems as single diastereomers in good overall yields.

Entities:  

Mesh：

Substances：

Year:  2013        PMID： 23311620      PMCID： PMC3562701          DOI： 10.1021/jo302734w

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  29 in total

1.  Organometallic enantiomeric scaffolding: a strategy for the enantiocontrolled construction of regio- and stereodivergent trisubstituted piperidines from a common precursor.

Authors:  Heilam Wong; Ethel C Garnier-Amblard; Lanny S Liebeskind
Journal:  J Am Chem Soc       Date:  2011-04-22       Impact factor: 15.419

2.  Development of a 2-aza-Cope-[3 + 2] dipolar cycloaddition strategy for the synthesis of quaternary proline scaffolds.

Authors:  Michael P McCormack; Tamila Shalumova; Joseph M Tanski; Stephen P Waters
Journal:  Org Lett       Date:  2010-09-03       Impact factor: 6.005

3.  Semi-synthesis of 2-deoxo- and 3-epi-paraherquamide A.

Authors:  B H Lee; M F Clothier; S S Johnson
Journal:  Bioorg Med Chem Lett       Date:  2001-02-26       Impact factor: 2.823

4.  Synthesis of the asperparaline core by a radical cascade.

Authors:  Peter J Crick; Nigel S Simpkins; Adrian Highton
Journal:  Org Lett       Date:  2011-11-14       Impact factor: 6.005

5.  Novel antinematodal and antiparasitic agents from Penicillium charlesii. II. Structure determination of paraherquamides B, C, D, E, F, and G.

Authors:  J M Liesch; C F Wichmann
Journal:  J Antibiot (Tokyo)       Date:  1990-11       Impact factor: 2.649

6.  An aza-Prins cyclization approach to functionalized indolizidines from 2-allylpyrrolidines.

Authors:  Xiaoxi Liu; Michael P McCormack; Stephen P Waters
Journal:  Org Lett       Date:  2012-10-25       Impact factor: 6.005

7.  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

Review 8.  Indolizidine and quinolizidine alkaloids.

Authors:  Joseph P Michael
Journal:  Nat Prod Rep       Date:  2002-12       Impact factor: 13.423

9.  Iron-catalyzed, hydrogen-mediated reductive cyclization of 1,6-enynes and diynes: evidence for bis(imino)pyridine ligand participation.

Authors:  Kevin T Sylvester; Paul J Chirik
Journal:  J Am Chem Soc       Date:  2009-07-01       Impact factor: 15.419

10.  Stereocontrolled cyclic nitrone cycloaddition strategy for the synthesis of pyrrolizidine and indolizidine alkaloids.

Authors:  Alberto Brandi; Francesca Cardona; Stefano Cicchi; Franca M Cordero; Andrea Goti
Journal:  Chemistry       Date:  2009-08-10       Impact factor: 5.236
View more
  2 in total

1.  Lewis acidic FeCl3 promoted 2-aza-Cope rearrangement to afford α-substituted homoallylamines in dimethyl carbonate.

Authors:  Karthik Gadde; Jonas Daelemans; Bert U W Maes; Kourosch Abbaspour Tehrani
Journal:  RSC Adv       Date:  2019-06-07       Impact factor: 3.361

2.  A new entry to azomethine ylides from allylic amines and glyoxals: shifting the reliance on amino ester precursors.

Authors:  Natalie K Machamer; Xiaoxi Liu; Stephen P Waters
Journal:  Org Lett       Date:  2014-09-23       Impact factor: 6.005
  2 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.