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Literature DB >> 23530855

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

Abstract

A highly diastereoselective synthesis of N-acetyl dihydrotetrafibricin methyl ester (34) is described. The synthesis features three enantioselective double allylboration reactions and an intramolecular hydrosilylation/Fleming-n class="Chemical">Tamao oxidation sequence to establish seven of the hydroxy-bearing stereocenters of 34. Especially noteworthy is the fragment-assembly double allyboration reaction of 2 and 7 using reagent 3, which provides the advanced intermediate 6 with >20:1 diastereoselectivity.

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Year: 2013 PMID： 23530855 PMCID： PMC3679187 DOI： 10.1021/ja401918r

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

19 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. 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. 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. 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

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. 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

7. 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

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. Stereoselective synthesis of syn,syn- and syn,anti-1,3,5-triols via intramolecular hydrosilylation of substituted pent-3-en-1,5-diols.

Authors: Fangzheng Li; William R Roush
Journal: Org Lett Date: 2009-07-02 Impact factor: 6.005

4 in total

4. Enantioselective synthesis of (Z)- and (E)-2-methyl-1,5-anti-pentenediols via an allene hydroboration-double-allylboration reaction sequence.

Authors: Ming Chen; William R Roush
Journal: J Am Chem Soc Date: 2013-06-12 Impact factor: 15.419