Literature DB >> 21524078

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

Tyler J Harrison1, Stephen Ho, James L Leighton.   

Abstract

A highly efficient and step-economical synthesis of zincophorin methyl ester has been achieved. The unprecedented step economy of this zincophorin synthesis is principally due to an application of the tandem silylformylation-crotylsilylation/Tamao oxidation-diastereoselective tautomerization reaction, which achieves in a single step what would typically require a significant multistep sequence.
© 2011 American Chemical Society

Entities:  

Mesh:

Substances:

Year:  2011        PMID: 21524078      PMCID: PMC3092851          DOI: 10.1021/ja201467z

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


  30 in total

1.  Tandem Intramolecular Alkyne Silylformylation-Allylsilylation: A Case of Remote 1,5-Asymmetric Induction Financial support was provided by the National Institutes of Health (National Institute of General Medical Sciences, GM58133). We are grateful to Bristol-Myers Squibb for generous financial support in the form of an Unrestricted Grant in Synthetic Organic Chemistry to J.L.L. We thank Merck Research Laboratories and DuPont Pharmaceuticals for generous financial support.

Authors:  Steven J. O'Malley; James L. Leighton
Journal:  Angew Chem Int Ed Engl       Date:  2001-08-03       Impact factor: 15.336

Review 2.  On the remarkable antitumor properties of fludelone: how we got there.

Authors:  Alexey Rivkin; Ting-Chao Chou; Samuel J Danishefsky
Journal:  Angew Chem Int Ed Engl       Date:  2005-05-06       Impact factor: 15.336

Review 3.  Advances in the total synthesis of biologically important marine macrolides.

Authors:  Kap-Sun Yeung; Ian Paterson
Journal:  Chem Rev       Date:  2005-12       Impact factor: 60.622

4.  Enantioselective synthesis of oasomycin A, part III: fragment assembly and confirmation of structure.

Authors:  David A Evans; Pavel Nagorny; Kenneth J McRae; Louis-Sebastian Sonntag; Dominic J Reynolds; Filisaty Vounatsos
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

5.  A formal total synthesis of (+)-zincophorin. Observation of an unusual urea-directed Stork-Crabtree hydrogenation.

Authors:  Zhenlei Song; Richard P Hsung
Journal:  Org Lett       Date:  2007-05-05       Impact factor: 6.005

6.  Cyclofunctionalization and free-radical-based hydrogen-transfer reactions. An iterative reaction sequence applied to the synthesis of the C(7)-C(16) subunit of zincophorin.

Authors:  Y Guindon; L Murtagh; V Caron; S R Landry; G Jung; M Bencheqroun; A M Faucher; B Guérin
Journal:  J Org Chem       Date:  2001-08-10       Impact factor: 4.354

7.  Griseochelin, a novel carboxylic acid antibiotic from Streptomyces griseus.

Authors:  U Gräfe; W Schade; M Roth; L Radics; M Incze; K Ujszászy
Journal:  J Antibiot (Tokyo)       Date:  1984-08       Impact factor: 2.649

8.  Organocatalytic asymmetric epoxidation of olefins by chiral ketones.

Authors:  Yian Shi
Journal:  Acc Chem Res       Date:  2004-08       Impact factor: 22.384

9.  Total synthesis of zincophorin and its methyl ester.

Authors:  Magali Defosseux; Nicolas Blanchard; Christophe Meyer; Janine Cossy
Journal:  J Org Chem       Date:  2004-07-09       Impact factor: 4.354

Review 10.  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

View more
  12 in total

1.  Organic chemistry: reactions at the end of a tether.

Authors:  Stefan Roesner; Varinder K Aggarwal
Journal:  Nature       Date:  2012-07-05       Impact factor: 49.962

2.  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

3.  Direct generation of acyclic polypropionate stereopolyads via double diastereo- and enantioselective iridium-catalyzed crotylation of 1,3-diols: beyond stepwise carbonyl addition in polyketide construction.

Authors:  Xin Gao; Hoon Han; Michael J Krische
Journal:  J Am Chem Soc       Date:  2011-07-25       Impact factor: 15.419

4.  Local Desymmetrization through Diastereotopic Group Selection: An Enabling Strategy for Natural Product Synthesis.

Authors:  Matthew A Horwitz; Jeffrey S Johnson
Journal:  European J Org Chem       Date:  2017-02-07

5.  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

6.  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

7.  Reiterative epoxide-based strategies for the synthesis of stereo-n-ads and application to polypropionate synthesis. A Personal Account.

Authors:  Alejandra Cruz-Montañez; Keyla F Morales-Rivera; Wildeliz Torres; Elizabeth M Valentín; Jaileen Rentas; José A Prieto
Journal:  Inorganica Chim Acta       Date:  2017-06-15       Impact factor: 2.545

8.  A highly step-economical synthesis of dictyostatin.

Authors:  Stephen Ho; Cyril Bucher; James L Leighton
Journal:  Angew Chem Int Ed Engl       Date:  2013-05-10       Impact factor: 15.336

9.  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

10.  An "aprotic" Tamao oxidation/syn-selective tautomerization reaction for the efficient synthesis of the C1-C9 fragment of fludelone.

Authors:  Tyler J Harrison; Philippe M A Rabbat; James L Leighton
Journal:  Org Lett       Date:  2012-09-05       Impact factor: 6.005

View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.