Literature DB >> 20958036

Total synthesis of isokidamycin.

B Michael O'Keefe1, Douglas M Mans, David E Kaelin, Stephen F Martin.   

Abstract

The synthesis of isokidamycin, which represents the first total synthesis of a bis-C-aryl glycoside natural product in the pluramycin family, has been completed. The synthesis features the use of a silicon tether as a disposable regiocontrol element in an intramolecular Diels-Alder reaction between a substituted naphthyne and a glycosyl furan and a subsequent O→C-glycoside rearrangement.

Entities:  

Mesh：

Substances：

Year:  2010        PMID： 20958036      PMCID： PMC2974561          DOI： 10.1021/ja107926f

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


  12 in total

1.  General strategies for the synthesis of the major classes of C-aryl glycosides.

Authors:  D E Kaelin; O D Lopez; S F Martin
Journal:  J Am Chem Soc       Date:  2001-07-18       Impact factor: 15.419

2.  A new antitumor antibiotic, kidamycin. II. Experimental treatment of cancer with kidamycin.

Authors:  N Kanda; M Kono; K Asano
Journal:  J Antibiot (Tokyo)       Date:  1972-10       Impact factor: 2.649

3.  A new antitumor antibiotic, kidamycin. I. Isolation, purification and properties of kidamycin.

Authors:  N Kanda
Journal:  J Antibiot (Tokyo)       Date:  1971-09       Impact factor: 2.649

4.  Stereoselective synthesis of vancosamine and saccharosamine glycals via tungsten-catalyzed alkynol cycloisomerization.

Authors:  William W Cutchins; Frank E McDonald
Journal:  Org Lett       Date:  2002-03-07       Impact factor: 6.005

5.  Regioselective synthesis of unsymmetrical C-aryl glycosides using silicon tethers as disposable linkers.

Authors:  David E Kaelin; Steven M Sparks; Hilary R Plake; Stephen F Martin
Journal:  J Am Chem Soc       Date:  2003-10-29       Impact factor: 15.419

6.  First total synthesis of a polyunsaturated chromone metabolite isolated from the brown algae Zonaria tournefortii.

Authors:  Hany F Anwar; Trond Vidar Hansen
Journal:  Org Lett       Date:  2009-02-05       Impact factor: 6.005

7.  Carbonylative cross-coupling of ortho-disubstituted aryl iodides. convenient synthesis of sterically hindered aryl ketones.

Authors:  B Michael O'Keefe; Nicholas Simmons; Stephen F Martin
Journal:  Org Lett       Date:  2008-10-24       Impact factor: 6.005

8.  Stereo- and regioselective glycosylations to the bis-C-arylglycoside of kidamycin.

Authors:  ZhongBo Fei; Frank E McDonald
Journal:  Org Lett       Date:  2007-08-11       Impact factor: 6.005

9.  Tandem Intramolecular Benzyne-Furan Cycloadditions. Total Synthesis of Vineomycinone B(2) Methyl Ester.

Authors:  Steven M Sparks; Chi-Li Chen; Stephen F Martin
Journal:  Tetrahedron       Date:  2007-08-27       Impact factor: 2.457

10.  Deacetylation effect of N,N-dimethylvancosamine in saptomycins D and E.

Authors:  N Abe; N Enoki; Y Nakakita; H Uchida; T Nakamura; M Munekata
Journal:  J Antibiot (Tokyo)       Date:  1993-04       Impact factor: 2.649
View more
  11 in total

1.  Ruthenium(0) Catalyzed Endiyne-α-Ketol [4 + 2] Cycloaddition: Convergent Assembly of Type II Polyketide Substructures via C-C Bond Forming Transfer Hydrogenation.

Authors:  Aakarsh Saxena; Felix Perez; Michael J Krische
Journal:  J Am Chem Soc       Date:  2015-05-04       Impact factor: 15.419

2.  Studies Toward the Syntheses of Pluramycin Natural Products. The First Total Synthesis of Isokidamycin.

Authors:  B Michael O'Keefe; Douglas M Mans; David E Kaelin; Stephen F Martin
Journal:  Tetrahedron       Date:  2011-09-02       Impact factor: 2.457

3.  Facile Access to Sterically Hindered Aryl Ketones via Carbonylative Cross-Coupling: Application to the Total Synthesis of Luteolin.

Authors:  B Michael O'Keefe; Nicholas Simmons; Stephen F Martin
Journal:  Tetrahedron       Date:  2011-06-17       Impact factor: 2.457

4.  Natural Products and Their Mimics as Targets of Opportunity for Discovery.

Authors:  Stephen F Martin
Journal:  J Org Chem       Date:  2017-09-15       Impact factor: 4.354

5.  Studies toward the total synthesis of pluraflavin A.

Authors:  John Hartung; Benjamin J D Wright; Samuel J Danishefsky
Journal:  Chemistry       Date:  2014-06-12       Impact factor: 5.236

6.  Tandem Electrocyclic Ring Opening/Radical Cyclization: Application to the Total Synthesis of Cribrostatin 6.

Authors:  Daniel Knueppel; Stephen F Martin
Journal:  Tetrahedron       Date:  2011-12-23       Impact factor: 2.457

7.  Approach toward the total synthesis of 5-hydroxyaloin A.

Authors:  Kristen J Procko; Hui Li; Stephen F Martin
Journal:  Org Lett       Date:  2010-11-17       Impact factor: 6.005

8.  Ruthenium(0)-Catalyzed [4+2] Cycloaddition of Acetylenic Aldehydes with α-Ketols: Convergent Construction of Angucycline Ring Systems.

Authors:  Aakarsh Saxena; Felix Perez; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2015-12-09       Impact factor: 15.336

9.  Enantioselective Ruthenium-Catalyzed Benzocyclobutenone-Ketol Cycloaddition: Merging C-C Bond Activation and Transfer Hydrogenative Coupling for Type II Polyketide Construction.

Authors:  Brett R Ambler; Ben W H Turnbull; Sankar Rao Suravarapu; Maulen M Uteuliyev; Nancy O Huynh; Michael J Krische
Journal:  J Am Chem Soc       Date:  2018-07-11       Impact factor: 15.419

10.  Photoassisted diversity-oriented synthesis: accessing 2,6-epoxyazocane (oxamorphan) cores.

Authors:  Olga A Mukhina; N N Bhuvan Kumar; Teresa M Cowger; Andrei G Kutateladze
Journal:  J Org Chem       Date:  2014-11-05       Impact factor: 4.354
View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.