Literature DB >> 16836397

Total synthesis and stereochemistry of pinnatoxins B and C.

Fumiyoshi Matsuura1, Junliang Hao, Reinhard Reents, Yoshito Kishi.   

Abstract

[Structure: see text] Pinnatoxins B and C were synthesized from diols (34R)-3b and (34S)-3a, respectively, in a stereochemically controlled manner. Through extensive analysis of the 1H NMR spectra of synthetic PnTXs B and C, the diagnostic NMR signals were first identified to differentiate (34S)- and (34R)-diastereomers and then used to establish the C34 configuration of natural PnTXs B and C as 34S and 34R, respectively.

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Year:  2006        PMID： 16836397      PMCID： PMC2532836          DOI： 10.1021/ol0611548

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


  6 in total

1.  A stereoselective synthesis of the C10-C31 (BCDEF ring) portion of pinnatoxin A.

Authors:  S Nakamura; J Inagaki; T Sugimoto; M Kudo; M Nakajima; S Hashimoto
Journal:  Org Lett       Date:  2001-12-13       Impact factor: 6.005

2.  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

3.  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

4.  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

5.  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

6.  Efficient ring-opening reaction of epoxides and aziridines promoted by tributylphosphine in water.

Authors:  Ren-Hua Fan; Xue-Long Hou
Journal:  J Org Chem       Date:  2003-02-07       Impact factor: 4.354
  6 in total
  5 in total

1.  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

Review 2.  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

3.  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

4.  Studies toward the synthesis of spirolides: assembly of the elaborated E-ring fragment.

Authors:  Craig E Stivala; Armen Zakarian
Journal:  Org Lett       Date:  2009-02-19       Impact factor: 6.005

Review 5.  Potential Threats Posed by New or Emerging Marine Biotoxins in UK Waters and Examination of Detection Methodologies Used for Their Control: Cyclic Imines.

Authors:  Keith Davidson; Clothilde Baker; Cowan Higgins; Wendy Higman; Sarah Swan; Andrea Veszelovszki; Andrew D Turner
Journal:  Mar Drugs       Date:  2015-11-26       Impact factor: 5.118
  5 in total

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