Literature DB >> 18163635

Total synthesis of 7-deoxypancratistatin-1-carboxaldehyde and carboxylic acid via solvent-free intramolecular aziridine opening: phenanthrene to phenanthridone cyclization strategy.

Jonathan Collins1, Melissa Drouin, Xuetong Sun, Uwe Rinner, Tomas Hudlicky.   

Abstract

Solid-state silica-gel-catalyzed opening of aziridine 6 provided phenanthrene 7, whose oxidative cleavage, recyclization, and further elaboration furnished the C-1 aldehyde and carboxylic acid derivatives of 7-deoxypancratistatin for potential analogue synthesis.

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Year:  2007        PMID： 18163635     DOI： 10.1021/ol702440f

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


  6 in total

1.  Chemoenzymatic synthesis of Amaryllidaceae constituents and biological evaluation of their C-1 analogues. The next generation synthesis of 7-deoxypancratistatin and trans-dihydrolycoricidine.

Authors:  Jonathan Collins; Uwe Rinner; Michael Moser; Tomas Hudlicky; Ion Ghiviriga; Anntherese E Romero; Alexander Kornienko; Dennis Ma; Carly Griffin; Siyaram Pandey
Journal:  J Org Chem       Date:  2010-05-07       Impact factor: 4.354

2.  Synthesis of C-1 homologues of pancratistatin and their preliminary biological evaluation.

Authors:  Sergey Vshyvenko; Jon Scattolon; Tomas Hudlicky; Anntherese E Romero; Alexander Kornienko
Journal:  Bioorg Med Chem Lett       Date:  2011-06-22       Impact factor: 2.823

3.  Unnatural C-1 homologues of pancratistatin - Synthesis and promising biological activities.

Authors:  Sergey Vshyvenko; Jon Scattolon; Tomas Hudlicky; Anntherese E Romero; Alexander Kornienko; Dennis Ma; Ian Tuffley; Siyaram Pandey
Journal:  Can J Chem       Date:  2012-09-19       Impact factor: 1.118

4.  Antineoplastic agents. 454. Synthesis of the strong cancer cell growth inhibitors trans-dihydronarciclasine and 7-deoxy-trans-dihydronarciclasine (1a).

Authors:  George R Pettit; Sylvie Ducki; Stephen A Eastham; Noeleen Melody
Journal:  J Nat Prod       Date:  2009-07       Impact factor: 4.050

Review 5.  The role of biocatalysis in the asymmetric synthesis of alkaloids.

Authors:  Joerg H Schrittwieser; Verena Resch
Journal:  RSC Adv       Date:  2013-08-07       Impact factor: 3.361

6.  Stereoselective synthesis of trans-dihydronarciclasine derivatives containing a 1,4-benzodioxane moiety.

Authors:  Gábor Varró; Balázs Pogrányi; Alajos Grün; András Simon; László Hegedűs; István Kádas
Journal:  Monatsh Chem       Date:  2018-10-26       Impact factor: 1.451
  6 in total

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