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Literature DB >> 21469726

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

Esa T T Kumpulainen¹, Byungsoo Kang, Michael J Krische.

Abstract

The C(21)-C(40) fragment of fibrinogen receptor inhibitor tetrafibricin was prepared in 12 steps from propane diol (longest linear sequence). In this approach, 6 C-C bonds are formed via asymmetric iridium catalyzed transfer hydrogenative carbonyl allylation and 2 C═C bonds are formed via Grubbs olefin cross-metathesis.

Entities: Chemical Disease Species

Mesh：

Substances：

Year: 2011 PMID： 21469726 PMCID： PMC3084888 DOI： 10.1021/ol200735r

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

29 in total

1. Regioselective cross-metathesis reaction induced by steric hindrance.

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

2. Formation of C-C Bonds via Catalytic Hydrogenation and Transfer Hydrogenation: Vinylation, Allylation, and Enolate Addition of Carbonyl Compounds and Imines.

Authors: Ryan L Patman; John F Bower; In Su Kim; Michael J Krische
Journal: Aldrichimica Acta Date: 2008 Impact factor: 3.667

Review 3. Dehydrogenation as a substrate-activating strategy in homogeneous transition-metal catalysis.

Authors: Graham E Dobereiner; Robert H Crabtree
Journal: Chem Rev Date: 2010-02-10 Impact factor: 60.622

4. Hydrogen autotransfer in the N-alkylation of amines and related compounds using alcohols and amines as electrophiles.

Authors: Gabriela Guillena; Diego J Ramón; Miguel Yus
Journal: Chem Rev Date: 2010-03-10 Impact factor: 60.622

5. 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

6. 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

7. 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

8. 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

9. Cross-dehydrogenative coupling (CDC): exploring C-C bond formations beyond functional group transformations.

Authors: Chao-Jun Li
Journal: Acc Chem Res Date: 2009-02-17 Impact factor: 22.384

10. Concise synthesis of the bryostatin A-ring via consecutive C-C bond forming transfer hydrogenations.

Authors: Yu Lu; Michael J Krische
Journal: Org Lett Date: 2009-07-16 Impact factor: 6.005

4 in total

1. 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