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Literature DB >> 25313264

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

Abstract

A concise synthesis of 4,5-epi-11-hydroxy-saxitoxinol utilizing D-ribose to direct an asymmetric Mannich reaction. This approach allows many modes of reactivity, which can be used to access various analogs of saxitoxin.

Entities: CellLine Chemical Disease Species

Keywords: Diamino acid; Mannich reaction; Saxitoxin; Sodium channel; Zetekitoxin AB

Year: 2014 PMID： 25313264 PMCID： PMC4192658 DOI： 10.1016/j.tet.2014.08.058

Source DB: PubMed Journal: Tetrahedron ISSN： 0040-4020 Impact factor: 2.457

11 in total

1. Total synthesis of (+)-decarbamoylsaxitoxin and (+)-gonyautoxin 3.

Authors: Osamu Iwamoto; Kazuo Nagasawa
Journal: Org Lett Date: 2010-05-07 Impact factor: 6.005

2. A synthetic route to the saxitoxin skeleton: synthesis of decarbamoyl α-saxitoxinol, an analogue of saxitoxin produced by the cyanobacterium Lyngbya wollei.

Authors: Yusuke Sawayama; Toshio Nishikawa
Journal: Angew Chem Int Ed Engl Date: 2011-06-17 Impact factor: 15.336

3. Alpha-amido sulfones as stable precursors of reactive N-acylimino derivatives.

Authors: Marino Petrini
Journal: Chem Rev Date: 2005-11 Impact factor: 60.622

4. 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

5. Highly diastereoselective addition of nitromethane anion to chiral alpha-amidoalkylphenyl sulfones. Synthesis of optically active alpha-amino acid derivatives.

Authors: Elisabetta Foresti; Gianni Palmieri; Marino Petrini; Roberto Profeta
Journal: Org Biomol Chem Date: 2003-10-23 Impact factor: 3.876

6. The structure of zetekitoxin AB, a saxitoxin analog from the Panamanian golden frog Atelopus zeteki: a potent sodium-channel blocker.

Authors: Mari Yotsu-Yamashita; Yong H Kim; Samuel C Dudley; Gaurav Choudhary; Arnold Pfahnl; Yasukatsu Oshima; John W Daly
Journal: Proc Natl Acad Sci U S A Date: 2004-03-22 Impact factor: 11.205

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

1. Total synthesis of (+)-decarbamoylsaxitoxin and (+)-gonyautoxin 3.

2. A synthetic route to the saxitoxin skeleton: synthesis of decarbamoyl α-saxitoxinol, an analogue of saxitoxin produced by the cyanobacterium Lyngbya wollei.

3. Alpha-amido sulfones as stable precursors of reactive N-acylimino derivatives.

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

5. Highly diastereoselective addition of nitromethane anion to chiral alpha-amidoalkylphenyl sulfones. Synthesis of optically active alpha-amino acid derivatives.

6. The structure of zetekitoxin AB, a saxitoxin analog from the Panamanian golden frog Atelopus zeteki: a potent sodium-channel blocker.

7. Total synthesis of (-)- and (+)-decarbamoyloxysaxitoxin and (+)-saxitoxin.

8. (+)-saxitoxin: a first and second generation stereoselective synthesis.

9. A synthesis of (+)-saxitoxin.

10. A stereoselective synthesis of (+)-gonyautoxin 3.

1. Preparation of a 1,2-isoxazolidine synthon for the synthesis of zetekitoxin AB.