Literature DB >> 21755949

Synthesis of the macrocyclic core of leiodermatolide.

Ian Paterson1, Tanya Paquet, Stephen M Dalby.   

Abstract

The macrocyclic core (2) of the marine macrolide leiodermatolide (1) has been synthesized in 19 steps through a convergent strategy exploiting boron aldol methodology to install the requisite stereochemistry and a selective Stille coupling reaction for controlled fragment assembly, followed by a Yamaguchi macrolactonization and carbamate introduction at the C9-OH.
© 2011 American Chemical Society

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Year:  2011        PMID： 21755949     DOI： 10.1021/ol2017388

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  7 in total

1.  Synthesis, Structural Reassignment, and Antibacterial Evaluation of 2,18-Seco-Lankacidinol B.

Authors:  Yanmin Yao; Lingchao Cai; Ian B Seiple
Journal:  Angew Chem Int Ed Engl       Date:  2018-09-11       Impact factor: 15.336

2.  Analogues of the Potent Antitumor Compound Leiodermatolide from a Deep-Water Sponge of the Genus Leiodermatium.

Authors:  Amy E Wright; Jill C Roberts; Esther A Guzmán; Tara P Pitts; Shirley A Pomponi; John K Reed
Journal:  J Nat Prod       Date:  2017-01-30       Impact factor: 4.050

Review 3.  Challenges and discoveries in the total synthesis of complex polyketide natural products.

Authors:  Ian Paterson; Nelson Yuen Sum Lam
Journal:  J Antibiot (Tokyo)       Date:  2017-10-25       Impact factor: 2.649

4.  Total synthesis of the antimitotic marine macrolide (-)-leiodermatolide.

Authors:  Ian Paterson; Kenneth K-H Ng; Simon Williams; David C Millican; Stephen M Dalby
Journal:  Angew Chem Int Ed Engl       Date:  2014-01-30       Impact factor: 15.336

Review 5.  Catalytic enantioselective synthesis of chiral organic compounds of ultra-high purity of >99% ee.

Authors:  Ei-ichi Negishi; Shiqing Xu
Journal:  Proc Jpn Acad Ser B Phys Biol Sci       Date:  2015       Impact factor: 3.493

6.  Total Synthesis of Leiodermatolide A via Transfer Hydrogenative Allylation, Crotylation, and Propargylation: Polyketide Construction beyond Discrete Allyl- or Allenylmetal Reagents.

Authors:  Yuk-Ming Siu; James Roane; Michael J Krische
Journal:  J Am Chem Soc       Date:  2021-07-08       Impact factor: 16.383

7.  Synthesis of the C(1)-C(13) Fragment of Leiodermatolide via Hydrogen-Mediated C-C Bond Formation.

Authors:  James Roane; Julian Wippich; Stephen D Ramgren; Michael J Krische
Journal:  Org Lett       Date:  2017-11-23       Impact factor: 6.005
  7 in total

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