Literature DB >> 15816769

An approach to the imine ring system of pinnatoxins.

Matthew J Pelc1, Armen Zakarian.   

Abstract

[reaction: see text] A concise stereoselective approach to the spirobicyclic imine fragment of pinnatoxins and pteriatoxins is described. The approach relies on a tandem reaction sequence involving consecutive sigmatropic rearrangements to build the quaternary chiral center at the core of the spirobicyclic ring system.

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Year:  2005        PMID： 15816769     DOI： 10.1021/ol050321l

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


  5 in total

1.  Unified total synthesis of pteriatoxins and their diastereomers.

Authors:  Fumiyoshi Matsuura; René Peters; Masahiro Anada; Scott S Harried; Junliang Hao; Yoshito Kishi
Journal:  J Am Chem Soc       Date:  2006-06-14       Impact factor: 15.419

Review 2.  Synthesis and biology of cyclic imine toxins, an emerging class of potent, globally distributed marine toxins.

Authors:  Craig E Stivala; Evelyne Benoit; Rómulo Aráoz; Denis Servent; Alexei Novikov; Jordi Molgó; Armen Zakarian
Journal:  Nat Prod Rep       Date:  2015-03       Impact factor: 13.423

3.  Total synthesis and stereochemistry of pinnatoxins B and C.

Authors:  Fumiyoshi Matsuura; Junliang Hao; Reinhard Reents; Yoshito Kishi
Journal:  Org Lett       Date:  2006-07-20       Impact factor: 6.005

4.  Total synthesis of pinnatoxins A and G and revision of the mode of action of pinnatoxin A.

Authors:  Romulo Araoz; Denis Servent; Jordi Molgó; Bogdan I Iorga; Carole Fruchart-Gaillard; Evelyne Benoit; Zhenhua Gu; Craig Stivala; Armen Zakarian
Journal:  J Am Chem Soc       Date:  2011-06-17       Impact factor: 15.419

5.  Marine Toxins with Spiroimine Rings: Total Synthesis of Pinnatoxin A.

Authors:  Stéphane Beaumont; Elizabeth A Ilardi; Nicholas D C Tappin; Armen Zakarian
Journal:  European J Org Chem       Date:  2010-10-01
  5 in total

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