Literature DB >> 20141163

Stereoselective synthesis of a monocyclic peloruside a analogue.

Christoph W Wullschleger1, Jürg Gertsch, Karl-Heinz Altmann.   

Abstract

The stereoselective synthesis of the monocyclic peloruside A analogue 4 has been achieved, following a new efficient approach for the introduction of the side chain, involving a late-stage addition of vinyl lithium species 7a to aldehyde 8. Further key steps are a highly diastereoselective allyltitanation reaction and a RCM-based macrocyclization.

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Year:  2010        PMID: 20141163     DOI: 10.1021/ol100123p

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


  5 in total

1.  Total synthesis of peloruside A through kinetic lactonization and relay ring-closing metathesis cyclization reactions.

Authors:  Thomas R Hoye; Junha Jeon; Lucas C Kopel; Troy D Ryba; Manomi A Tennakoon; Yini Wang
Journal:  Angew Chem Int Ed Engl       Date:  2010-08-16       Impact factor: 15.336

Review 2.  Conformation-activity relationships of polyketide natural products.

Authors:  Erik M Larsen; Matthew R Wilson; Richard E Taylor
Journal:  Nat Prod Rep       Date:  2015-08       Impact factor: 13.423

3.  Evans Enolates: Solution Structures of Lithiated Oxazolidinone-Derived Enolates.

Authors:  Evan H Tallmadge; David B Collum
Journal:  J Am Chem Soc       Date:  2015-10-05       Impact factor: 15.419

4.  Rapid access to conformational analogues of (+)-peloruside A.

Authors:  Zhiming Zhao; Richard E Taylor
Journal:  Org Lett       Date:  2012-01-11       Impact factor: 6.005

5.  Total synthesis of (-)-18-epi-peloruside A: an alkyne linchpin strategy.

Authors:  Barry M Trost; David J Michaelis; Sushant Malhotra
Journal:  Org Lett       Date:  2013-10-04       Impact factor: 6.005

  5 in total

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