Literature DB >> 15987219

Total synthesis of quinolizidine alkaloid (-)-217A. Application of iminoacetonitrile cycloadditions in organic synthesis.

Kevin M Maloney1, Rick L Danheiser.   

Abstract

[reaction: see text] An intramolecular iminoacetonitrile [4 + 2] cycloaddition functions as the key step in an efficient total synthesis of the quinolizidine alkaloid (-)-217A.

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Year:  2005        PMID： 15987219      PMCID： PMC3203637          DOI： 10.1021/ol051185n

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  11 in total

1.  Recent developments in olefin cross-metathesis.

Authors:  Stephen J Connon; Siegfried Blechert
Journal:  Angew Chem Int Ed Engl       Date:  2003-04-29       Impact factor: 15.336

2.  Intramolecular [4 + 2] cycloadditions of iminoacetonitriles: a new class of azadienophiles for hetero Diels-Alder reactions.

Authors:  David T Amos; Adam R Renslo; Rick L Danheiser
Journal:  J Am Chem Soc       Date:  2003-04-30       Impact factor: 15.419

3.  A 1,4-disubstituted quinolizidine from a Madagascan mantelline frog (Mantella).

Authors:  P Jain; H M Garraffo; H J Yeh; T F Spande; J W Daly; N R Andriamaharavo; M Andriantsiferana
Journal:  J Nat Prod       Date:  1996-12       Impact factor: 4.050

4.  Total Synthesis of (+)-Halichlorine: An Inhibitor of VCAM-1 Expression.

Authors: 
Journal:  Angew Chem Int Ed Engl       Date:  1999-12-03       Impact factor: 15.336

5.  A general model for selectivity in olefin cross metathesis.

Authors:  Arnab K Chatterjee; Tae-Lim Choi; Daniel P Sanders; Robert H Grubbs
Journal:  J Am Chem Soc       Date:  2003-09-17       Impact factor: 15.419

Review 6.  Indolizidine and quinolizidine alkaloids.

Authors:  Joseph P Michael
Journal:  Nat Prod Rep       Date:  2004-09-14       Impact factor: 13.423

7.  Design, synthesis, and X-ray data of novel potential antipsychotic agents. Substituted 7-phenylquinolizidines: stereospecific, neuroleptic, and antinociceptive properties.

Authors:  R Imhof; E Kyburz; J J Daly
Journal:  J Med Chem       Date:  1984-02       Impact factor: 7.446

8.  A formal total synthesis of (+/-)-halichlorine and (+/-)-pinnaic acid.

Authors:  Yosuke Matsumura; Sakae Aoyagi; Chihiro Kibayashi
Journal:  Org Lett       Date:  2004-03-18       Impact factor: 6.005

9.  Alkaloids in Madagascan frogs (Mantella): pumiliotoxins, indolizidines, quinolizidines, and pyrrolizidines.

Authors:  H M Garraffo; J Caceres; J W Daly; T F Spande; N R Andriamaharavo; M Andriantsiferana
Journal:  J Nat Prod       Date:  1993-07       Impact factor: 4.050

10.  Highly enantioenriched tetrahydropyridines from chiral organosilanes: application to the synthesis of quinolizidine alkaloid (-)-217A.

Authors:  Hongbing Huang; Thomas F Spande; James S Panek
Journal:  J Am Chem Soc       Date:  2003-01-22       Impact factor: 15.419
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  2 in total

Review 1.  The reductive decyanation reaction: an overview and recent developments.

Authors:  Jean-Marc R Mattalia
Journal:  Beilstein J Org Chem       Date:  2017-02-13       Impact factor: 2.883

2.  Analogues of amphibian alkaloids: total synthesis of (5R,8S,8aS)-(-)-8-methyl-5-pentyloctahydroindolizine (8-epi-indolizidine 209B) and [(1S,4R,9aS)-(-)-4-pentyloctahydro-2H-quinolizin-1-yl]methanol.

Authors:  Joseph P Michael; Claudia Accone; Charles B de Koning; Christiaan W van der Westhuyzen
Journal:  Beilstein J Org Chem       Date:  2008-01-18       Impact factor: 2.883
  2 in total

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