Literature DB >> 17286378

Diastereoselective synthesis of the pectenotoxin 2 non-anomeric AB spiroacetal.

Danielle Vellucci1, Scott D Rychnovsky.   

Abstract

The reductive cyclization reaction of a cyanoacetal has been used to prepare the pectenotoxin 2 (PTX-2) AB spiroacetal with high diastereoselectively for the first time. The strategy is convergent and makes use of the axial-selective reductive lithiation of 2-cyano tetrahydropyran rings to introduce the spiroacetal center with the desired non-anomeric selectivity. [reaction: see text].

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Year:  2007        PMID： 17286378      PMCID： PMC2487677          DOI： 10.1021/ol0630447

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


  18 in total

1.  Asymmetric syntheses of pectenotoxins-4 and -8, part I: synthesis of the C1-C19 subunit.

Authors:  David A Evans; Hemaka A Rajapakse; Dirk Stenkamp
Journal:  Angew Chem Int Ed Engl       Date:  2002-12-02       Impact factor: 15.336

Review 2.  Nonanomeric spiroketals in natural products: structures, sources, and synthetic strategies.

Authors:  Jatta E Aho; Petri M Pihko; Terhi K Rissa
Journal:  Chem Rev       Date:  2005-12       Impact factor: 60.622

3.  Stereocontrolled synthesis of spiroketals via a remarkable methanol-induced kinetic spirocyclization reaction.

Authors:  Justin S Potuzak; Sirkka B Moilanen; Derek S Tan
Journal:  J Am Chem Soc       Date:  2005-10-12       Impact factor: 15.419

4.  Studies on the synthesis of pectenotoxin II: synthesis of a C(11)-C(26) fragment precursor via [3 + 2]-annulation reactions of chiral allylsilanes.

Authors:  G C Micalizio; W R Roush
Journal:  Org Lett       Date:  2001-06-14       Impact factor: 6.005

5.  An aldol approach to the synthesis of the EF fragment of spongistatin 1.

Authors:  M T Crimmins; J D Katz; L C McAtee; E A Tabet; S J Kirincich
Journal:  Org Lett       Date:  2001-03-22       Impact factor: 6.005

6.  Oocyte-based screening of cytokinesis inhibitors and identification of pectenotoxin-2 that induces Bim/Bax-mediated apoptosis in p53-deficient tumors.

Authors:  Hee-Don Chae; Tae-Saeng Choi; Byeong-Mo Kim; Jee H Jung; Yung-Jue Bang; Deug Y Shin
Journal:  Oncogene       Date:  2005-07-14       Impact factor: 9.867

7.  Determination of pectenotoxin-2 after solid-phase extraction from seawater and from the dinoflagellate Dinophysis fortii by liquid chromatography with electrospray mass spectrometry and ultraviolet detection. Evidence of oxidation of pectenotoxin-2 to pectenotoxin-6 in scallops.

Authors:  T Suzuki; T Mitsuya; H Matsubara; M Yamasaki
Journal:  J Chromatogr A       Date:  1998-07-31       Impact factor: 4.759

8.  Characterization of F-actin depolymerization as a major toxic event induced by pectenotoxin-6 in neuroblastoma cells.

Authors:  Francisco Leira; Ana G Cabado; Mercedes R Vieytes; Yolanda Roman; Amparo Alfonso; Luis M Botana; Takeshi Yasumoto; Claudia Malaguti; Gian P Rossini
Journal:  Biochem Pharmacol       Date:  2002-06-01       Impact factor: 5.858

9.  Stereocontrolled synthesis of spiroketals via Ti(Oi-Pr)4-mediated kinetic spirocyclization of glycal epoxides with retention of configuration.

Authors:  Sirkka B Moilanen; Justin S Potuzak; Derek S Tan
Journal:  J Am Chem Soc       Date:  2006-02-15       Impact factor: 15.419

10.  Synthesis of the ABC tricyclic fragment of the pectenotoxins via stereocontrolled cyclization of a gamma-hydroxyepoxide appended to the AB spiroacetal unit.

Authors:  Rosliana Halim; Margaret A Brimble; Jörn Merten
Journal:  Org Biomol Chem       Date:  2006-03-01       Impact factor: 3.876
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  5 in total

1.  A convergent route to the CDEF-tetracycle of pectenotoxin-2.

Authors:  Daniel P Canterbury; Glenn C Micalizio
Journal:  Org Lett       Date:  2011-04-08       Impact factor: 6.005

2.  Spirodiepoxide strategy to the C ring of pectenotoxin 4: synthesis of the C1-C19 sector.

Authors:  Sipak Joyasawal; Stephen D Lotesta; N G Akhmedov; Lawrence J Williams
Journal:  Org Lett       Date:  2010-03-05       Impact factor: 6.005

3.  Synthesis of the C1-C26 hexacyclic subunit of pectenotoxin 2.

Authors:  Ozora Kubo; Daniel P Canterbury; Glenn C Micalizio
Journal:  Org Lett       Date:  2012-10-26       Impact factor: 6.005

4.  Function-Oriented Studies Targeting Pectenotoxin 2: Synthesis of the GH-Ring System and a Structurally Simplified Macrolactone.

Authors:  Natasha F O'Rourke; Mu A; Henry N Higgs; Alan Eastman; Glenn C Micalizio
Journal:  Org Lett       Date:  2017-09-13       Impact factor: 6.005

Review 5.  Recent synthetic approaches toward non-anomeric spiroketals in natural products.

Authors:  Sylvain Favre; Pierre Vogel; Sandrine Gerber-Lemaire
Journal:  Molecules       Date:  2008       Impact factor: 4.411
  5 in total

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