Literature DB >> 29992811

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

Brett R Ambler1, Ben W H Turnbull1, Sankar Rao Suravarapu1, Maulen M Uteuliyev1, Nancy O Huynh1, Michael J Krische1.   

Abstract

The first enantioselective intermolecular metal-catalyzed cycloadditions of benzocyclobutenones via C-C bond oxidative addition are described. In the presence of a ruthenium(0) complex modified by ( R)-DM-SEGPHOS, tetralone-derived ketols and benzocyclobutenones combine to form cycloadducts with complete regio- and diastereoselectivity and high enantioselectivity. Using this method, the "bay region" substructure of the angucycline natural product arenimycin was prepared.

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Year:  2018        PMID： 29992811      PMCID： PMC6226000          DOI： 10.1021/jacs.8b05724

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


  60 in total

1.  Total syntheses of HMP-Y1, hibarimicinone, and HMP-P1.

Authors:  Brian B Liau; Benjamin C Milgram; Matthew D Shair
Journal:  J Am Chem Soc       Date:  2012-09-26       Impact factor: 15.419

2.  Predictive compound accumulation rules yield a broad-spectrum antibiotic.

Authors:  Michelle F Richter; Bryon S Drown; Andrew P Riley; Alfredo Garcia; Tomohiro Shirai; Riley L Svec; Paul J Hergenrother
Journal:  Nature       Date:  2017-05-10       Impact factor: 49.962

3.  Ruthenium-catalyzed insertion of adjacent diol carbon atoms into C-C bonds: Entry to type II polyketides.

Authors:  Matthias Bender; Ben W H Turnbull; Brett R Ambler; Michael J Krische
Journal:  Science       Date:  2017-08-25       Impact factor: 47.728

4.  A single step approach to piperidines via Ni-catalyzed β-carbon elimination.

Authors:  Puneet Kumar; Janis Louie
Journal:  Org Lett       Date:  2012-04-02       Impact factor: 6.005

5.  Diols, α-Ketols, and Diones as 22π Components in [2+2+2] Cycloadditions of 1,6-Diynes via Ruthenium(0)-Catalyzed Transfer Hydrogenation.

Authors:  Hiroki Sato; Matthias Bender; Weijie Chen; Michael J Krische
Journal:  J Am Chem Soc       Date:  2016-12-09       Impact factor: 15.419

6.  Total synthesis of isokidamycin.

Authors:  B Michael O'Keefe; Douglas M Mans; David E Kaelin; Stephen F Martin
Journal:  J Am Chem Soc       Date:  2010-11-10       Impact factor: 15.419

7.  SF2446, new benzo[a]naphthacene quinone antibiotics. II. The structural elucidation.

Authors:  S Gomi; T Sasaki; J Itoh; M Sezaki
Journal:  J Antibiot (Tokyo)       Date:  1988-04       Impact factor: 2.649

8.  Successive C-C coupling of dienes to vicinally dioxygenated hydrocarbons: ruthenium catalyzed [4 + 2] cycloaddition across the diol, hydroxycarbonyl, or dione oxidation levels.

Authors:  Laina M Geary; Ben W Glasspoole; Mary M Kim; Michael J Krische
Journal:  J Am Chem Soc       Date:  2013-02-28       Impact factor: 15.419

9.  Ruthenium-catalyzed hydrohydroxyalkylation of acrylates with diols and α-hydroxycarbonyl compounds to form spiro- and α-methylene-γ-butyrolactones.

Authors:  Emma L McInturff; Jeffrey Mowat; Andrew R Waldeck; Michael J Krische
Journal:  J Am Chem Soc       Date:  2013-11-05       Impact factor: 15.419

10.  Carbon-carbon bond activation of cyclobutenones enabled by the addition of chiral organocatalyst to ketone.

Authors:  Bao-Sheng Li; Yuhuang Wang; Zhichao Jin; Pengcheng Zheng; Rakesh Ganguly; Yonggui Robin Chi
Journal:  Nat Commun       Date:  2015-02-05       Impact factor: 14.919
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  4 in total

1.  Controlling the Cleavage of Carbon-Carbon Bonds To Generate α,α-Difluorobenzyl Carbanions for the Construction of Difluoromethylbenzenes.

Authors:  Hari R Khatri; Changho Han; Erica Luong; Xiaoliang Pan; Amna T Adam; Maali D Alshammari; Yihan Shao; David A Colby
Journal:  J Org Chem       Date:  2019-09-06       Impact factor: 4.354

Review 2.  Ruthenium-Catalyzed Cycloadditions to Form Five-, Six-, and Seven-Membered Rings.

Authors:  Rosalie S Doerksen; Tomáš Hodík; Guanyu Hu; Nancy O Huynh; William G Shuler; Michael J Krische
Journal:  Chem Rev       Date:  2021-02-12       Impact factor: 60.622

3.  Catalytic Asymmetric Synthesis of Cyclohexanes by Hydrogen Borrowing Annulations.

Authors:  Roly J Armstrong; Wasim M Akhtar; Tom A Young; Fernanda Duarte; Timothy J Donohoe
Journal:  Angew Chem Int Ed Engl       Date:  2019-08-07       Impact factor: 15.336

4.  An endo-Directing-Group Strategy Unlocks Enantioselective (3+1+2) Carbonylative Cycloadditions of Aminocyclopropanes.

Authors:  Olga O Sokolova; John F Bower
Journal:  Angew Chem Int Ed Engl       Date:  2022-06-24       Impact factor: 16.823
  4 in total

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