Literature DB >> 15230584

Total synthesis of zincophorin and its methyl ester.

Magali Defosseux1, Nicolas Blanchard, Christophe Meyer, Janine Cossy.   

Abstract

A total synthesis of the naturally occurring ionophore zincophorin has been realized. The route features an intramolecular oxymercuration of a cyclopropanemethanol and a Carroll-Claisen rearrangement for the respective elaboration of the C1-C12 and C13-C25 subunits, which have been assembled by using a highly diastereoselective titanium-mediated aldol condensation.

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Year:  2004        PMID： 15230584     DOI： 10.1021/jo0496042

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  9 in total

1.  Evolution of an Efficient and Scalable Nine-Step (Longest Linear Sequence) Synthesis of Zincophorin Methyl Ester.

Authors:  Liang-An Chen; Melissa A Ashley; James L Leighton
Journal:  J Am Chem Soc       Date:  2017-03-15       Impact factor: 15.419

2.  Studies on a urea-directed Stork-Crabtree hydrogenation. Synthesis of the C1-C9 subunit of (+)-zincophorin.

Authors:  Zhenlei Song; Richard P Hsung; Ting Lu; Andrew G Lohse
Journal:  J Org Chem       Date:  2007-11-03       Impact factor: 4.354

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.  Highly stereoselective synthesis of anti,anti-dipropionate stereotriads: a solution to the long-standing problem of challenging mismatched double asymmetric crotylboration reactions.

Authors:  Ming Chen; William R Roush
Journal:  J Am Chem Soc       Date:  2012-02-14       Impact factor: 15.419

5.  Direct Generation of Triketide Stereopolyads via Merged Redox-Construction Events: Total Synthesis of (+)-Zincophorin Methyl Ester.

Authors:  Zachary A Kasun; Xin Gao; Radoslaw M Lipinski; Michael J Krische
Journal:  J Am Chem Soc       Date:  2015-07-13       Impact factor: 15.419

6.  Toward more "ideal" polyketide natural product synthesis: a step-economical synthesis of zincophorin methyl ester.

Authors:  Tyler J Harrison; Stephen Ho; James L Leighton
Journal:  J Am Chem Soc       Date:  2011-04-27       Impact factor: 15.419

Review 7.  Challenges in the synthesis of a unique mono-carboxylic acid antibiotic, (+)-zincophorin.

Authors:  Zhenlei Song; Andrew G Lohse; Richard P Hsung
Journal:  Nat Prod Rep       Date:  2009-04       Impact factor: 13.423

8.  Enantioselective Alcohol C-H Functionalization for Polyketide Construction: Unlocking Redox-Economy and Site-Selectivity for Ideal Chemical Synthesis.

Authors:  Jiajie Feng; Zachary A Kasun; Michael J Krische
Journal:  J Am Chem Soc       Date:  2016-04-26       Impact factor: 15.419

9.  Tandem silylformylation-crotylsilylation/Tamao oxidation of internal alkynes: a remarkable example of generating complexity from simplicity.

Authors:  Jared T Spletstoser; Michael J Zacuto; James L Leighton
Journal:  Org Lett       Date:  2008-12-18       Impact factor: 6.005
  9 in total

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