Literature DB >> 23464668

Total synthesis of 6-deoxyerythronolide B via C-C bond-forming transfer hydrogenation.

Xin Gao1, Sang Kook Woo, Michael J Krische.   

Abstract

The 14-membered macrolide 6-deoxyerythronolide B is prepared in 14 steps (longest linear sequence) and 20 total steps. Two different methods for alcohol CH-crotylation via transfer hydrogenation are deployed for the first time in target-oriented synthesis. Enyne metathesis is used to form the 14-membered ring. The present approach represents the most concise construction of any erythronolide reported, to date.

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Year:  2013        PMID: 23464668      PMCID: PMC3625983          DOI: 10.1021/ja4008722

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


  33 in total

1.  An abiotic strategy for the enantioselective synthesis of erythromycin B.

Authors:  Paul J Hergenrother; Anne Hodgson; Andrew S Judd; Wen-Cherng Lee; Stephen F Martin
Journal:  Angew Chem Int Ed Engl       Date:  2003-07-21       Impact factor: 15.336

2.  Catalytic asymmetric synthesis of complex polypropionates: Lewis base catalyzed aldol equivalents in the synthesis of erythronolide B.

Authors:  Binita Chandra; Dezhi Fu; Scott G Nelson
Journal:  Angew Chem Int Ed Engl       Date:  2010-03-29       Impact factor: 15.336

Review 3.  Macrolides. Recent progress in chemistry and biochemistry.

Authors:  S Masamune; G S Bates; J W Corcoran
Journal:  Angew Chem Int Ed Engl       Date:  1977-09       Impact factor: 15.336

4.  Unlocking Hydrogenation for C-C Bond Formation: A Brief Overview of Enantioselective Methods.

Authors:  Abbas Hassan; Michael J Krische
Journal:  Org Process Res Dev       Date:  2011-11-18       Impact factor: 3.317

Review 5.  Modern aldol methods for the total synthesis of polyketides.

Authors:  Bernd Schetter; Rainer Mahrwald
Journal:  Angew Chem Int Ed Engl       Date:  2006-11-20       Impact factor: 15.336

6.  Total synthesis of bryostatin 7 via C-C bond-forming hydrogenation.

Authors:  Yu Lu; Sang Kook Woo; Michael J Krische
Journal:  J Am Chem Soc       Date:  2011-08-11       Impact factor: 15.419

7.  Total synthesis of 10-deoxymethynolide and narbonolide.

Authors:  Richeng Xuan; Hong-Se Oh; Younghoon Lee; Han-Young Kang
Journal:  J Org Chem       Date:  2008-01-19       Impact factor: 4.354

8.  Recent advances in the activation of boron and silicon reagents for stereocontrolled allylation reactions.

Authors:  Jason W J Kennedy; Dennis G Hall
Journal:  Angew Chem Int Ed Engl       Date:  2003-10-13       Impact factor: 15.336

9.  Ammonia free partial reduction of aromatic compounds using lithium di-tert-butylbiphenyl (LiDBB).

Authors:  Timothy J Donohoe; David House
Journal:  J Org Chem       Date:  2002-07-12       Impact factor: 4.354

10.  Ruthenium-catalyzed C-C bond forming transfer hydrogenation: carbonyl allylation from the alcohol or aldehyde oxidation level employing acyclic 1,3-dienes as surrogates to preformed allyl metal reagents.

Authors:  Fumitoshi Shibahara; John F Bower; Michael J Krische
Journal:  J Am Chem Soc       Date:  2008-04-29       Impact factor: 15.419

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  23 in total

1.  Total Synthesis of Swinholide A: An Exposition in Hydrogen-Mediated C-C Bond Formation.

Authors:  Inji Shin; Suckchang Hong; Michael J Krische
Journal:  J Am Chem Soc       Date:  2016-10-25       Impact factor: 15.419

Review 2.  Asymmetric Iridium-Catalyzed C-C Coupling of Chiral Diols via Site-Selective Redox-Triggered Carbonyl Addition.

Authors:  Inji Shin; Michael J Krische
Journal:  Top Curr Chem       Date:  2016

3.  Formal Synthesis of Premisakinolide A and C(19)-C(32) of Swinholide A via Site-Selective C-H Allylation and Crotylation of Unprotected Diols.

Authors:  Inji Shin; Michael J Krische
Journal:  Org Lett       Date:  2015-10-02       Impact factor: 6.005

Review 4.  Feedstock Reagents in Metal-Catalyzed Carbonyl Reductive Coupling: Minimizing Preactivation for Efficiency in Target-Oriented Synthesis.

Authors:  Rosalie S Doerksen; Cole C Meyer; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2019-07-26       Impact factor: 15.336

5.  Total Synthesis of Clavosolide A via Asymmetric Alcohol-Mediated Carbonyl Allylation: Beyond Protecting Groups or Chiral Auxiliaries in Polyketide Construction.

Authors:  James M Cabrera; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2019-06-24       Impact factor: 15.336

6.  Asymmetric alcohol C-H allylation and syn-crotylation: C9-C20 of tetrafibricin.

Authors:  Takahiko Itoh; T Patrick Montgomery; Antonio Recio; Michael J Krische
Journal:  Org Lett       Date:  2014-01-14       Impact factor: 6.005

7.  Biocatalytic synthesis of pikromycin, methymycin, neomethymycin, novamethymycin, and ketomethymycin.

Authors:  Douglas A Hansen; Christopher M Rath; Eli B Eisman; Alison R H Narayan; Jeffrey D Kittendorf; Jonathan D Mortison; Yeo Joon Yoon; David H Sherman
Journal:  J Am Chem Soc       Date:  2013-07-18       Impact factor: 15.419

8.  Total synthesis of (+)-trienomycins A and F via C-C bond-forming hydrogenation and transfer hydrogenation.

Authors:  David J Del Valle; Michael J Krische
Journal:  J Am Chem Soc       Date:  2013-07-17       Impact factor: 15.419

Review 9.  Catalytic enantioselective C-H functionalization of alcohols by redox-triggered carbonyl addition: borrowing hydrogen, returning carbon.

Authors:  John M Ketcham; Inji Shin; T Patrick Montgomery; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2014-07-23       Impact factor: 15.336

Review 10.  Polyketide construction via hydrohydroxyalkylation and related alcohol C-H functionalizations: reinventing the chemistry of carbonyl addition.

Authors:  Anne-Marie R Dechert-Schmitt; Daniel C Schmitt; Xin Gao; Takahiko Itoh; Michael J Krische
Journal:  Nat Prod Rep       Date:  2014-02-11       Impact factor: 13.423

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