Literature DB >> 17249805

Stereoselective synthesis of the C(1)-C(19) fragment of tetrafibricin.

Ricardo Lira1, William R Roush.   

Abstract

[reaction: see text] A stereoselective synthesis of the C(1)-C(19) fragment of tetrafibricin has been accomplished via a highly diastereoselective double allylboration reaction of 6-8 and an iodonium ion promoted urethane cyclization for the installation of the C(15) alkoxy function in 3.

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Year:  2007        PMID： 17249805      PMCID： PMC2701644          DOI： 10.1021/ol0629869

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


  9 in total

1.  Complete stereochemistry of tetrafibricin.

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

2.  Synthesis of the C(43)-C(67) fragment of amphidinol 3.

Authors:  Jacqueline D Hicks; Eric M Flamme; William R Roush
Journal:  Org Lett       Date:  2005-11-24       Impact factor: 6.005

3.  Enantioselective synthesis of 1,5-anti- and 1,5-syn-diols using a highly diastereoselective one-pot double allylboration reaction sequence.

Authors:  Eric M Flamme; William R Roush
Journal:  J Am Chem Soc       Date:  2002-11-20       Impact factor: 15.419

4.  Synthesis of the C(1)-C(25) fragment of amphidinol 3: application of the double-allylboration reaction for synthesis of 1,5-diols.

Authors:  Eric M Flamme; William R Roush
Journal:  Org Lett       Date:  2005-03-31       Impact factor: 6.005

5.  Tetrafibricin: synthesis of the C1-C13, C15-C25, and C27-C40 fragments.

Authors:  Samir BouzBouz; Janine Cossy
Journal:  Org Lett       Date:  2004-09-30       Impact factor: 6.005

6.  Tetrafibricin: a nonpeptidic fibrinogen receptor inhibitor from Streptomyces neyagawaensis. (II). Its antiplatelet activities.

Authors:  T Satoh; Y Yamashita; T Kamiyama; M Arisawa
Journal:  Thromb Res       Date:  1993-12-01       Impact factor: 3.944

7.  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

8.  Tetrafibricin has a high selectivity for GPIIb/IIIa: comparison of the effects of tetrafibricin and RGDS on GPIIb/IIIa and the vitronectin receptor.

Authors:  T Satoh; W C Kouns; Y Yamashita; T Kamiyama; B Steiner
Journal:  Biochem Biophys Res Commun       Date:  1994-10-14       Impact factor: 3.575

9.  Synthesis of 2,6-trans-disubstituted 5,6-dihydropyrans from (Z)-1,5-syn-endiols.

Authors:  Eric M Flamme; William R Roush
Journal:  Beilstein J Org Chem       Date:  2005-08-26       Impact factor: 2.883
  9 in total
  14 in total

1.  Efficient and selective syntheses of (all-E)- and (6E,10Z)-2'-O-methylmyxalamides D via Pd-catalyzed alkenylation--carbonyl olefination synergy.

Authors:  Guangwei Wang; Zhihong Huang; Ei-Ichi Negishi
Journal:  Org Lett       Date:  2008-07-02       Impact factor: 6.005

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

Authors:  Kai Zhang; Dennis P Curran
Journal:  Synlett       Date:  2010-03-01       Impact factor: 2.454

3.  Total synthesis of (+)-roxaticin via C-C bond forming transfer hydrogenation: a departure from stoichiometric chiral reagents, auxiliaries, and premetalated nucleophiles in polyketide construction.

Authors:  Soo Bong Han; Abbas Hassan; In Su Kim; Michael J Krische
Journal:  J Am Chem Soc       Date:  2010-11-10       Impact factor: 15.419

4.  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

5.  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

6.  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

7.  Enantioselective synthesis of 2-methyl-1,2-syn- and 2-methyl-1,2-anti-3-butenediols via allene hydroboration-aldehyde allylboration reaction sequences.

Authors:  Ming Chen; Masaki Handa; William R Roush
Journal:  J Am Chem Soc       Date:  2009-10-21       Impact factor: 15.419

8.  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

9.  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

10.  Concerning the selective protection of (Z)-1,5-syn-ene-diols and (E)-1,5-anti-ene-diols as allylic triethylsilyl ethers.

Authors:  Jacqueline D Hicks; Chan Woo Huh; Ashley D Legg; William R Roush
Journal:  Org Lett       Date:  2007-11-21       Impact factor: 6.005
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