Literature DB >> 20686632

Fluorous Mixture Synthesis of Four Stereoisomers of the C21-C40 Fragment of Tetrafibricin.

Kai Zhang1, Dennis P Curran.   

Abstract

Four stereoisomers of the C21-C40 fragment are synthesized in a single exercise with the aid of fluorous tagging to encode configurations at C37 and C33. After demixing and detagging, the isomers were found to have substantially identical (1)H NMR spectra. However, there were some small but reliable differences in their (13)C NMR spectra.

Entities:  

Year:  2010        PMID： 20686632      PMCID： PMC2914344          DOI： 10.1055/s-0029-1219376

Source DB:  PubMed          Journal:  Synlett        ISSN： 0936-5214            Impact factor:   2.454


  18 in total

1.  Solution-phase preparation of a 560-compound library of individual pure mappicine analogues by fluorous mixture synthesis.

Authors:  Wei Zhang; Zhiyong Luo; Christine Hiu-Tung Chen; Dennis P Curran
Journal:  J Am Chem Soc       Date:  2002-09-04       Impact factor: 15.419

2.  Complete stereochemistry of tetrafibricin.

Authors:  Yoshihisa Kobayashi; Werngard Czechtizky; Yoshito Kishi
Journal:  Org Lett       Date:  2003-01-09       Impact factor: 6.005

3.  Quasienantiomers and quasiracemates: new tools for identification, analysis, separation, and synthesis of enantiomers.

Authors:  Qisheng Zhang; Dennis P Curran
Journal:  Chemistry       Date:  2005-08-19       Impact factor: 5.236

4.  Combinatorial synthesis of the 1,5-polyol system based on cross metathesis: structure revision of amphidinol 3.

Authors:  Tohru Oishi; Mitsunori Kanemoto; Respati Swasono; Nobuaki Matsumori; Michio Murata
Journal:  Org Lett       Date:  2008-10-30       Impact factor: 6.005

5.  Highly selective hydrolytic kinetic resolution of terminal epoxides catalyzed by chiral (salen)Co(III) complexes. Practical synthesis of enantioenriched terminal epoxides and 1,2-diols.

Authors:  Scott E Schaus; Bridget D Brandes; Jay F Larrow; Makoto Tokunaga; Karl B Hansen; Alexandra E Gould; Michael E Furrow; Eric N Jacobsen
Journal:  J Am Chem Soc       Date:  2002-02-20       Impact factor: 15.419

6.  Fluorous mixture synthesis: a fluorous-tagging strategy for the synthesis and separation of mixtures of organic compounds.

Authors:  Z Luo; Q Zhang; Y Oderaotoshi; D P Curran
Journal:  Science       Date:  2001-03-02       Impact factor: 47.728

7.  Total synthesis of polycavernoside A, a lethal toxin of the red alga Polycavernosa tsudai.

Authors:  Paul R Blakemore; Cindy C Browder; Jian Hong; Christopher M Lincoln; Pavel A Nagornyy; Lonnie A Robarge; Duncan J Wardrop; James D White
Journal:  J Org Chem       Date:  2005-07-08       Impact factor: 4.354

8.  A practical and efficient synthesis of the C-16-C-28 spiroketal fragment (CD) of the spongistatins.

Authors:  Matthew J Gaunt; David F Hook; Huw R Tanner; Steven V Ley
Journal:  Org Lett       Date:  2003-12-11       Impact factor: 6.005

9.  Tetrafibricin, a novel fibrinogen receptor antagonist. I. Taxonomy, fermentation, isolation, characterization and biological activities.

Authors:  T Kamiyama; T Umino; N Fujisaki; K Fujimori; T Satoh; Y Yamashita; S Ohshima; J Watanabe; K Yokose
Journal:  J Antibiot (Tokyo)       Date:  1993-07       Impact factor: 2.649

10.  Tetrafibricin, a novel fibrinogen receptor antagonist. II. Structural elucidation.

Authors:  T Kamiyama; Y Itezono; T Umino; T Satoh; N Nakayama; K Yokose
Journal:  J Antibiot (Tokyo)       Date:  1993-07       Impact factor: 2.649
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  7 in total

1.  Synthesis of C1-C20 and C21-C40 fragments of tetrafibricin.

Authors:  Venugopal Gudipati; Dennis P Curran
Journal:  Tetrahedron Lett       Date:  2011-04-27       Impact factor: 2.415

2.  Enantio- and diastereoselective synthesis of (E)-1,5-syn-diols: application to the synthesis of the C(23)-C(40) fragment of tetrafibricin.

Authors:  Jeremy Kister; Philippe Nuhant; Ricardo Lira; Achim Sorg; William R Roush
Journal:  Org Lett       Date:  2011-03-04       Impact factor: 6.005

3.  Development of a Double Allylboration Reagent Targeting 1,5-syn-(E)-Diols: Application to the Synthesis of the C(23)-C(40) Fragment of Tetrafibricin.

Authors:  Philippe Nuhant; Jeremy Kister; Ricardo Lira; Achim Sorg; William R Roush
Journal:  Tetrahedron       Date:  2011-09-02       Impact factor: 2.457

4.  C(21)-C(40) of tetrafibricin via metal catalysis: beyond stoichiometric chiral reagents, auxiliaries, and premetalated nucleophiles.

Authors:  Esa T T Kumpulainen; Byungsoo Kang; Michael J Krische
Journal:  Org Lett       Date:  2011-04-06       Impact factor: 6.005

5.  Enantio- and diastereoselective synthesis of N-acetyl dihydrotetrafibricin methyl ester.

Authors:  Philippe Nuhant; William R Roush
Journal:  J Am Chem Soc       Date:  2013-03-26       Impact factor: 15.419

6.  Asymmetric alcohol C-H allylation and syn-crotylation: C9-C20 of tetrafibricin.

Authors:  Takahiko Itoh; T Patrick Montgomery; Antonio Recio; Michael J Krische
Journal:  Org Lett       Date:  2014-01-14       Impact factor: 6.005

7.  HiFSA fingerprinting applied to isomers with near-identical NMR spectra: the silybin/isosilybin case.

Authors:  José G Napolitano; David C Lankin; Tyler N Graf; J Brent Friesen; Shao-Nong Chen; James B McAlpine; Nicholas H Oberlies; Guido F Pauli
Journal:  J Org Chem       Date:  2013-03-05       Impact factor: 4.354
  7 in total

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