Literature DB >> 18759394

A stereoselective synthesis of (+)-gonyautoxin 3.

John V Mulcahy1, J Du Bois.   

Abstract

An asymmetric synthesis of the paralytic shellfish poison (PSP), (+)-gonyautoxin 3, is described. A unique, Rh-catalyzed amination reaction provides rapid access to the heteratom-rich, tricyclic core of the toxin, which is common to more than 30 related natural products. The completed route should facilitate the preparation of other naturally occurring PSPs and designed analogues thereof.

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Year:  2008        PMID： 18759394      PMCID： PMC2597710          DOI： 10.1021/ja805651g

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  15 in total

1.  Modeling P-loops domain of sodium channel: homology with potassium channels and interaction with ligands.

Authors:  Denis B Tikhonov; Boris S Zhorov
Journal:  Biophys J       Date:  2004-10-08       Impact factor: 4.033

2.  The pursuit of palau'amine.

Authors:  Matthias Köck; Achim Grube; Ian B Seiple; Phil S Baran
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3.  Tetrodotoxin, saxitoxin, and the molecular biology of the sodium channel.

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Journal:  Nat Toxins       Date:  1997

5.  Letter: Structures of gonyautoxin II and III from the East Coast toxic dinoflagellate Gonyaulax tamarensis.

Authors:  Y Shimizu; L J Buckley; M Alam; Y Oshima; W E Fallon; H Kasai; V P Miura IGullo
Journal:  J Am Chem Soc       Date:  1976-08-18       Impact factor: 15.419

6.  A stereospecific total synthesis of d,l-saxitoxin.

Authors:  H Tanino; T Nakata; T Kaneko; Y Kishi
Journal:  J Am Chem Soc       Date:  1977-04-13       Impact factor: 15.419

7.  Energetic localization of saxitoxin in its channel binding site.

Authors:  Gaurav Choudhary; Lisa Shang; Xiufeng Li; Samuel C Dudley
Journal:  Biophys J       Date:  2002-08       Impact factor: 4.033

8.  Actions of epimers of 12-(OH)-reduced saxitoxin and of 11-(OSO3)-saxitoxin on squid axon.

Authors:  C Y Kao; P N Kao; M R James-Kracke; F E Koehn; C F Wichmann; H K Schnoes
Journal:  Toxicon       Date:  1985       Impact factor: 3.033

9.  A synthesis of (+)-saxitoxin.

Authors:  James J Fleming; J Du Bois
Journal:  J Am Chem Soc       Date:  2006-03-29       Impact factor: 15.419

10.  Expanding the substrate scope for C-H amination reactions: oxidative cyclization of urea and guanidine derivatives.

Authors:  Mihyong Kim; John V Mulcahy; Christine G Espino; J Du Bois
Journal:  Org Lett       Date:  2006-03-16       Impact factor: 6.005
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  19 in total

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Authors:  Paul M Wehn; J Du Bois
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

2.  Mutant cycle analysis with modified saxitoxins reveals specific interactions critical to attaining high-affinity inhibition of hNaV1.7.

Authors:  Rhiannon Thomas-Tran; J Du Bois
Journal:  Proc Natl Acad Sci U S A       Date:  2016-05-09       Impact factor: 11.205

3.  Stereoselective Synthesis of Cyclic Guanidines by Directed Diamination of Unactivated Alkenes.

Authors:  Artur K Mailyan; Kyle Young; Joanna L Chen; Bradley T Reid; Armen Zakarian
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4.  Syntheses of Cyclic Guanidine-Containing Natural Products.

Authors:  Yuyong Ma; Saptarshi De; Chuo Chen
Journal:  Tetrahedron       Date:  2015-02-25       Impact factor: 2.457

5.  Synthesis of Cyclic Guanidines Bearing N-Arylsulfonyl and N-Cyano Protecting Groups via Pd-Catalyzed Alkene Carboamination Reactions.

Authors:  Luke J Peterson; Jingyi Luo; John P Wolfe
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6.  Divergent Synthesis of Natural Derivatives of (+)-Saxitoxin Including 11-Saxitoxinethanoic Acid.

Authors:  James R Walker; Jeffrey E Merit; Rhiannon Thomas-Tran; Doris T Y Tang; J Du Bois
Journal:  Angew Chem Int Ed Engl       Date:  2019-01-02       Impact factor: 15.336

7.  Marked difference in saxitoxin and tetrodotoxin affinity for the human nociceptive voltage-gated sodium channel (Nav1.7) [corrected].

Authors:  James R Walker; Paul A Novick; William H Parsons; Malcolm McGregor; Jeff Zablocki; Vijay S Pande; J Du Bois
Journal:  Proc Natl Acad Sci U S A       Date:  2012-10-17       Impact factor: 11.205

8.  Synthetic studies towards Zetekitoxin AB: preparation of 4,5-epi-11-hydroxy-saxitoxinol.

Authors:  Aaron D Pearson; Robert M Williams
Journal:  Tetrahedron       Date:  2014-10-28       Impact factor: 2.457

9.  Synthesis of Cyclic Guanidines via Silver-Catalyzed Intramolecular Alkene Hydroamination Reactions of N-Allylguanidines.

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Journal:  Org Lett       Date:  2016-05-11       Impact factor: 6.005

10.  Synthesis of cyclic guanidines via Pd-catalyzed alkene carboamination.

Authors:  Blane P Zavesky; Nicholas R Babij; Jonathan A Fritz; John P Wolfe
Journal:  Org Lett       Date:  2013-10-22       Impact factor: 6.005
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