Literature DB >> 16268555

Systematic assignment of the configuration of flexible natural products by spectroscopic and computational methods: the bistramide C analysis.

Gérard Zuber1, Michael-Rock Goldsmith, Tamara D Hopkins, David N Beratan, Peter Wipf.   

Abstract

[reaction: see text] The combination of NMR NOE, chemical shift, and J-coupling measurements with molar rotation and circular dichroism (CD) determinations, including RI-DFT BP86/aug-cc-pVDZ calculations, reduced a candidate pool of 1024 possible stereoisomers of (+)-bistramide C to a single absolute configuration assignment for the 10 stereogenic carbons of the marine natural product.

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Year:  2005        PMID: 16268555     DOI: 10.1021/ol052154v

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


  5 in total

1.  Optical signatures of molecular dissymmetry: combining theory with experiments to address stereochemical puzzles.

Authors:  Parag Mukhopadhyay; Peter Wipf; David N Beratan
Journal:  Acc Chem Res       Date:  2009-06-16       Impact factor: 22.384

2.  INTEGRATED APPROACHES TO THE CONFIGURATIONAL ASSIGNMENT OF MARINE NATURAL PRODUCTS.

Authors:  Tadeusz F Molinski; Brandon I Morinaka
Journal:  Tetrahedron       Date:  2012-11-18       Impact factor: 2.457

3.  Enantioselective total synthesis of bistramide A.

Authors:  Michael T Crimmins; Amy C DeBaillie
Journal:  J Am Chem Soc       Date:  2006-04-19       Impact factor: 15.419

Review 4.  A selective account of effective paradigms and significant outcomes in the discovery of inspirational marine natural products.

Authors:  Koneni V Sashidhara; Kimberly N White; Phillip Crews
Journal:  J Nat Prod       Date:  2009-03-27       Impact factor: 4.050

5.  Synthesis of a 35-member stereoisomer library of bistramide A: evaluation of effects on actin state, cell cycle and tumor cell growth.

Authors:  Iwona E Wrona; Jason T Lowe; Thomas J Turbyville; Tanya R Johnson; Julien Beignet; John A Beutler; James S Panek
Journal:  J Org Chem       Date:  2009-03-06       Impact factor: 4.354

  5 in total

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