Literature DB >> 21461316

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

Stéphane Beaumont1, Elizabeth A Ilardi, Nicholas D C Tappin, Armen Zakarian.   

Abstract

This microreview provides a compilation of synthetic approaches and total syntheses of pinnatoxin A in a survey of the literature up to early 2010. Pinnatoxin A is the first discovered and representative member of a fascinating group of potent marine toxins that share a spiroimine subunit as a unifying structural element.

Entities:  

Year:  2010        PMID： 21461316      PMCID： PMC3066085          DOI： 10.1002/ejoc.201000842

Source DB:  PubMed          Journal:  European J Org Chem        ISSN： 1099-0690


  22 in total

1.  A formal total synthesis of (+)-pinnatoxin A.

Authors:  Satoshi Sakamoto; Hayato Sakazaki; Koji Hagiwara; Kei Kamada; Kento Ishii; Takeshi Noda; Masayuki Inoue; Masahiro Hirama
Journal:  Angew Chem Int Ed Engl       Date:  2004-12-03       Impact factor: 15.336

2.  Stereochemistry of pteriatoxins A, B, and C.

Authors:  Junliang Hao; Fumiyoshi Matsuura; Yoshito Kishi; Masaki Kita; Daisuke Uemura; Naoki Asai; Takashi Iwashita
Journal:  J Am Chem Soc       Date:  2006-06-21       Impact factor: 15.419

3.  Acyclic stereocontrol in the Ireland-Claisen rearrangement of alpha-branched esters.

Authors:  Ying-chuan Qin; Craig E Stivala; Armen Zakarian
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

4.  An approach to the imine ring system of pinnatoxins.

Authors:  Matthew J Pelc; Armen Zakarian
Journal:  Org Lett       Date:  2005-04-14       Impact factor: 6.005

5.  Studies toward gymnodimine: development of a single-pot Hua reaction for the synthesis of highly hindered cyclic imines.

Authors:  Y Ahn; G I Cardenas; J Yang; D Romo
Journal:  Org Lett       Date:  2001-03-08       Impact factor: 6.005

Review 6.  Bivalve molluscs as vectors of marine biotoxins involved in seafood poisoning.

Authors:  P Ciminiello; E Fattorusso
Journal:  Prog Mol Subcell Biol       Date:  2006

7.  Biosynthesis of 13-desmethyl spirolide C by the dinoflagellate Alexandrium ostenfeldii.

Authors:  Shawna L MacKinnon; Allan D Cembella; Ian W Burton; Nancy Lewis; Patricia LeBlanc; John A Walter
Journal:  J Org Chem       Date:  2006-11-10       Impact factor: 4.354

8.  Isolation and structure of prorocentrolide B, a fast-acting toxin from Prorocentrum maculosum.

Authors:  T Hu; A S deFreitas; J M Curtis; Y Oshima; J A Walter; J L Wright
Journal:  J Nat Prod       Date:  1996-11       Impact factor: 4.050

9.  Enantioselective deprotonation by chiral lithium amide bases: asymmetric synthesis of trimethylsilyl enol ethers from 4-alkylcyclohexanones.

Authors:  R Shirai; M Tanaka; K Koga
Journal:  J Am Chem Soc       Date:  1986-02-01       Impact factor: 15.419

10.  4,6-O-benzylidene-D-glucopyranose and its sodium salt: new data on their preparation and properties.

Authors:  P L Barili; G Berti; G Catelani; C Cini; F D'Andrea; E Mastrorilli
Journal:  Carbohydr Res       Date:  1995-11-30       Impact factor: 2.104
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  8 in total

Review 1.  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

2.  Effect of counterion structure on rates and diastereoselectivities in α,β-unsaturated iminium-ion Diels-Alder reactions.

Authors:  David Marcoux; Pascal Bindschädler; Alexander W H Speed; Anna Chiu; Joseph E Pero; George A Borg; David A Evans
Journal:  Org Lett       Date:  2011-06-16       Impact factor: 6.005

3.  Studies toward the synthesis of spirolide C: exploration into the formation of the 23-membered all-carbon macrocyclic framework.

Authors:  Craig E Stivala; Zhenhua Gu; Lindsay L Smith; Armen Zakarian
Journal:  Org Lett       Date:  2012-01-19       Impact factor: 6.005

Review 4.  Cyclic imine toxins from dinoflagellates: a growing family of potent antagonists of the nicotinic acetylcholine receptors.

Authors:  Jordi Molgó; Pascale Marchot; Rómulo Aráoz; Evelyne Benoit; Bogdan I Iorga; Armen Zakarian; Palmer Taylor; Yves Bourne; Denis Servent
Journal:  J Neurochem       Date:  2017-03-21       Impact factor: 5.372

5.  Total synthesis of the spirocyclic imine marine toxin (-)-gymnodimine and an unnatural C4-epimer.

Authors:  Ke Kong; Ziad Moussa; Changsuk Lee; Daniel Romo
Journal:  J Am Chem Soc       Date:  2011-11-16       Impact factor: 15.419

6.  1,5-Hydrogen Atom Transfer/Surzur-Tanner Rearrangement: A Radical Cascade Approach for the Synthesis of 1,6-Dioxaspiro[4.5]decane and 6,8-Dioxabicyclo[3.2.1]octane Scaffolds in Carbohydrate Systems.

Authors:  Elisa I León; Ángeles Martín; Adrián S Montes; Inés Pérez-Martín; María Del Sol Rodríguez; Ernesto Suárez
Journal:  J Org Chem       Date:  2021-09-23       Impact factor: 4.354

Review 7.  Current Situation of Palytoxins and Cyclic Imines in Asia-Pacific Countries: Causative Phytoplankton Species and Seafood Poisoning.

Authors:  Young-Sang Kim; Hyun-Joo An; Jaeseong Kim; You-Jin Jeon
Journal:  Int J Environ Res Public Health       Date:  2022-04-18       Impact factor: 4.614

Review 8.  Emergent toxins in North Atlantic temperate waters: a challenge for monitoring programs and legislation.

Authors:  Marisa Silva; Vijaya K Pratheepa; Luis M Botana; Vitor Vasconcelos
Journal:  Toxins (Basel)       Date:  2015-03-16       Impact factor: 4.546
  8 in total

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