Literature DB >> 24422777

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

Takahiko Itoh1, T Patrick Montgomery, Antonio Recio, Michael J Krische.   

Abstract

The C9-C20 segment of the fibrinogen receptor inhibitor tetrafibricin was prepared in 10 steps (longest linear sequence). Ruthenium catalyzed enantioselective syn-crotylation is used to construct C9-C13. Iridium catalyzed asymmetric alcohol C-H allylation of a commercial malic acid derived alcohol is used to construct C14-C20. Recovery and recycling of the iridium catalyst is described.

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Year:  2014        PMID： 24422777      PMCID： PMC3932543          DOI： 10.1021/ol403566w

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


  36 in total

1.  Redox economy in organic synthesis.

Authors:  Noah Z Burns; Phil S Baran; Reinhard W Hoffmann
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

2.  Studies toward the synthesis of spirolide C: exploration into the formation of the 23-membered all-carbon macrocyclic framework.

Authors:  Craig E Stivala; Zhenhua Gu; Lindsay L Smith; Armen Zakarian
Journal:  Org Lett       Date:  2012-01-19       Impact factor: 6.005

3.  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

4.  Unlocking Hydrogenation for C-C Bond Formation: A Brief Overview of Enantioselective Methods.

Authors:  Abbas Hassan; Michael J Krische
Journal:  Org Process Res Dev       Date:  2011-11-18       Impact factor: 3.317

5.  Versatile configuration-encoded strategy for rapid synthesis of 1,5-polyol stereoisomers.

Authors:  Gregory K Friestad; Gopeekrishnan Sreenilayam
Journal:  Org Lett       Date:  2010-11-05       Impact factor: 6.005

6.  Total synthesis of bryostatin 7 via C-C bond-forming hydrogenation.

Authors:  Yu Lu; Sang Kook Woo; Michael J Krische
Journal:  J Am Chem Soc       Date:  2011-08-11       Impact factor: 15.419

7.  Tetrafibricin: a nonpeptidic fibrinogen receptor inhibitor from Streptomyces neyagawaensis (I). Its GPIIb/IIIa blockage on solid phase binding assay.

Authors:  T Satoh; Y Yamashita; T Kamiyama; J Watanabe; B Steiner; P Hadváry; M Arisawa
Journal:  Thromb Res       Date:  1993-12-01       Impact factor: 3.944

8.  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

9.  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

10.  Total synthesis of (+)-trienomycins A and F via C-C bond-forming hydrogenation and transfer hydrogenation.

Authors:  David J Del Valle; Michael J Krische
Journal:  J Am Chem Soc       Date:  2013-07-17       Impact factor: 15.419
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  1 in total

1.  Catalytic Enantioselective Carbonyl Allylation and Propargylation via Alcohol-Mediated Hydrogen Transfer: Merging the Chemistry of Grignard and Sabatier.

Authors:  Seung Wook Kim; Wandi Zhang; Michael J Krische
Journal:  Acc Chem Res       Date:  2017-08-09       Impact factor: 22.384
  1 in total

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