Literature DB >> 16524298

Studies in macrolide antibiotic synthesis: the role of tethered alkoxides in titanium alkoxide-mediated regioselective reductive coupling reactions.

Adilah B Bahadoor1, Glenn C Micalizio.   

Abstract

[reaction: see text] A convergent route to a C1-C15 fragment precursor for erythromycin-based macrolide antibiotics is presented. These studies define a role for tethered alkoxides in the control of site-selective carbon-carbon bond formation in titanium alkoxide-mediated coupling reactions of internal alkynes and chiral aldehydes.

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Year:  2006        PMID： 16524298     DOI： 10.1021/ol0600786

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


  8 in total

1.  Reaction design, discovery, and development as a foundation to function-oriented synthesis.

Authors:  Glenn C Micalizio; Sarah B Hale
Journal:  Acc Chem Res       Date:  2015-02-10       Impact factor: 22.384

2.  Regioselective Reductive Cross-Coupling Reactions of Unsymmetrical Alkynes.

Authors:  Holly A Reichard; Martin McLaughlin; Ming Z Chen; Glenn C Micalizio
Journal:  European J Org Chem       Date:  2010-01

3.  Enantioselective synthesis of anti- and syn-homopropargyl alcohols via chiral Brønsted acid catalyzed asymmetric allenylboration reactions.

Authors:  Ming Chen; William R Roush
Journal:  J Am Chem Soc       Date:  2012-06-25       Impact factor: 15.419

4.  A general strategy for regiocontrol in nickel-catalyzed reductive couplings of aldehydes and alkynes.

Authors:  Hasnain A Malik; Grant J Sormunen; John Montgomery
Journal:  J Am Chem Soc       Date:  2010-05-12       Impact factor: 15.419

5.  Highly diastereoselective preparation of anti-1,2-diols by catalytic addition of alkynylsilanes to alpha-silyloxyaldehydes.

Authors:  Kanicha Sa-ei; John Montgomery
Journal:  Org Lett       Date:  2006-09-28       Impact factor: 6.005

6.  Asymmetric synthesis of dihydroindanes by convergent alkoxide-directed metallacycle-mediated bond formation.

Authors:  Stephen N Greszler; Holly A Reichard; Glenn C Micalizio
Journal:  J Am Chem Soc       Date:  2012-01-31       Impact factor: 15.419

7.  The regio- and stereochemical course of reductive cross-coupling reactions between 1,3-disubstituted allenes and vinylsilanes: Synthesis of (Z)-dienes.

Authors:  Allan U Barlan; Glenn C Micalizio
Journal:  Tetrahedron       Date:  2010-06-26       Impact factor: 2.457

8.  Regiocontrol in catalytic reductive couplings through alterations of silane rate dependence.

Authors:  Evan P Jackson; John Montgomery
Journal:  J Am Chem Soc       Date:  2015-01-05       Impact factor: 15.419
  8 in total

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