Literature DB >> 16220936

Enantioselective syntheses of aeruginosin 298-A and its analogues using a catalytic asymmetric phase-transfer reaction and epoxidation.

Takashi Ohshima1, Vijay Gnanadesikan, Tomoyuki Shibuguchi, Yuhei Fukuta, Tetsuhiro Nemoto, Masakatsu Shibasaki.   

Abstract

We developed a versatile synthetic process for aeruginosin 298-A as well as several attractive analogues, in which all stereocenters were controlled by a catalytic asymmetric phase-transfer reaction and epoxidation. Furthermore, drastic counteranion effects in phase-transfer catalysis were observed for the first time, making it possible to three-dimensionally fine-tune the catalyst (ketal part, aromatic part, and counteranion).

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Year:  2003        PMID： 16220936     DOI： 10.1021/ja037290e

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


  10 in total

1.  A systematic investigation of quaternary ammonium ions as asymmetric phase-transfer catalysts. Synthesis of catalyst libraries and evaluation of catalyst activity.

Authors:  Scott E Denmark; Nathan D Gould; Larry M Wolf
Journal:  J Org Chem       Date:  2011-05-06       Impact factor: 4.354

2.  Synthesis of hydroxylated bicyclic amino acids from L-tyrosine: octahydro-1H-indole carboxylates.

Authors:  Joshua G Pierce; Dhanalakshmi Kasi; Makoto Fushimi; Anthony Cuzzupe; Peter Wipf
Journal:  J Org Chem       Date:  2008-09-04       Impact factor: 4.354

3.  Enantioselective syntheses and biological studies of aeruginosin 298-A and its analogs: application of catalytic asymmetric phase-transfer reaction.

Authors:  Yuhei Fukuta; Takashi Ohshima; Vijay Gnanadesikan; Tomoyuki Shibuguchi; Tetsuhiro Nemoto; Takaya Kisugi; Tatsufumi Okino; Masakatsu Shibasaki
Journal:  Proc Natl Acad Sci U S A       Date:  2004-03-02       Impact factor: 11.205

4.  Total synthesis of aeruginosin 98B.

Authors:  Barry M Trost; Toshiyuki Kaneko; Neil G Andersen; Christoph Tappertzhofen; Bruce Fahr
Journal:  J Am Chem Soc       Date:  2012-11-12       Impact factor: 15.419

5.  Investigations Concerning the Syntheses of TADDOL-Derived Secondary Amines and Their Use To Access Novel Chiral Organocatalysts.

Authors:  Katharina Gratzer; Mario Waser
Journal:  Synthesis (Stuttg)       Date:  2012-12       Impact factor: 3.157

6.  Aromatase and dual aromatase-steroid sulfatase inhibitors from the letrozole and vorozole templates.

Authors:  Paul M Wood; L W Lawrence Woo; Mark P Thomas; Mary F Mahon; Atul Purohit; Barry V L Potter
Journal:  ChemMedChem       Date:  2011-05-23       Impact factor: 3.466

7.  Syntheses and Applications of (Thio)Urea-Containing Chiral Quaternary Ammonium Salt Catalysts.

Authors:  Johanna Novacek; Mario Waser
Journal:  European J Org Chem       Date:  2014-02

8.  Isolation and Synthesis of Misszrtine A: A Novel Indole Alkaloid From Marine Sponge-Associated Aspergillus sp. SCSIO XWS03F03.

Authors:  Rong Zhou; Xiaojian Liao; Hangbin Li; Jing Li; Pengju Feng; BingXin Zhao; Shihai Xu
Journal:  Front Chem       Date:  2018-06-13       Impact factor: 5.221

9.  Application scope and limitations of TADDOL-derived chiral ammonium salt phase-transfer catalysts.

Authors:  Guddeangadi N Gururaja; Richard Herchl; Antonia Pichler; Katharina Gratzer; Mario Waser
Journal:  Molecules       Date:  2013-04-12       Impact factor: 4.411

10.  Towards Tartaric-Acid-Derived Asymmetric Organocatalysts.

Authors:  Katharina Gratzer; Guddeangadi N Gururaja; Mario Waser
Journal:  European J Org Chem       Date:  2013-06-03
  10 in total

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