Literature DB >> 16220183

Total synthesis of a diastereomer of the marine natural product clavosolide A.

Conor S Barry1, Nick Bushby, Jonathan P H Charmant, Jon D Elsworth, John R Harding, Christine L Willis.   

Abstract

The first total synthesis of the reported structure of the sponge metabolite clavosolide A is described using a Prins cyclisation to assemble the tetrahydropyran core followed by manipulation of the side-chain, dimerisation and finally glycosidation.

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Year:  2005        PMID: 16220183     DOI: 10.1039/b509757f

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN: 1359-7345            Impact factor:   6.222


  6 in total

1.  Racemization in Prins cyclization reactions.

Authors:  Ramesh Jasti; Scott D Rychnovsky
Journal:  J Am Chem Soc       Date:  2006-10-18       Impact factor: 15.419

2.  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

3.  Cyclopropane compatibility with oxidative carbocation formation: total synthesis of clavosolide A.

Authors:  GuangRong Peh; Paul E Floreancig
Journal:  Org Lett       Date:  2012-10-24       Impact factor: 6.005

4.  Discovery, Total Synthesis and Key Structural Elements for the Immunosuppressive Activity of Cocosolide, a Symmetrical Glycosylated Macrolide Dimer from Marine Cyanobacteria.

Authors:  Sarath P Gunasekera; Yang Li; Ranjala Ratnayake; Danmeng Luo; Jeannette Lo; Joseph H Reibenspies; Zhengshuang Xu; Michael J Clare-Salzler; Tao Ye; Valerie J Paul; Hendrik Luesch
Journal:  Chemistry       Date:  2016-05-03       Impact factor: 5.236

5.  Symmetric macrocycles by a Prins dimerization and macrocyclization strategy.

Authors:  Michael R Gesinski; Kwanruthai Tadpetch; Scott D Rychnovsky
Journal:  Org Lett       Date:  2009-11-19       Impact factor: 6.005

6.  Total Synthesis of Clavosolide A via Tandem Allylic Oxidation/Oxa-Conjugate Addition Reaction.

Authors:  Joseph B Baker; Hyoungsu Kim; Jiyong Hong
Journal:  Tetrahedron Lett       Date:  2015-06-03       Impact factor: 2.415

  6 in total

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