Literature DB >> 15987166

Configuration of the psymberin amide side chain.

Sezgin Kiren1, Lawrence J Williams.   

Abstract

[structure: see text] The structure of the amide side chain of psymberin, a potent and selective cytotoxin, is proposed. Syn and anti models of the amide side chain were prepared, and the structural assignment was confirmed by X-ray crystallographic analysis of the anti isomer. Comparison of (1)H and (13)C NMR data establishes homology between the natural product and the synthetic model compound of anti configuration and not the corresponding syn isomer.

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Year:  2005        PMID： 15987166     DOI： 10.1021/ol0508375

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


  8 in total

1.  Synthesis of psymberin analogues: probing a functional correlation with the pederin/mycalamide family of natural products.

Authors:  Xin Jiang; Noelle Williams; Jef K De Brabander
Journal:  Org Lett       Date:  2007-01-18       Impact factor: 6.005

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.  Asymmetric Synthesis of the C1-C6 Portion of the Psymberin Using an Evans Chiral Auxiliary.

Authors:  Ashutosh Pal; Zhenghong Peng; Paul T Schuber; Basvoju A Bhanu Prasad; William G Bornmann
Journal:  Tetrahedron Lett       Date:  2013-10-09       Impact factor: 2.415

4.  Total synthesis of (+)-psymberin (irciniastatin A): catalytic reagent control as the strategic cornerstone.

Authors:  Amos B Smith; Jon A Jurica; Shawn P Walsh
Journal:  Org Lett       Date:  2008-12-18       Impact factor: 6.005

5.  Progress toward the total synthesis of psymberin/irciniastatin A.

Authors:  Lauren E Brown; Yakira R Landaverry; James R Davies; Kristin A Milinkevich; Sandra Ast; Joseph S Carlson; Allen G Oliver; Joseph P Konopelski
Journal:  J Org Chem       Date:  2009-08-07       Impact factor: 4.354

6.  Studies toward the unique pederin family member psymberin: full structure elucidation, two alternative total syntheses, and analogs.

Authors:  Yu Feng; Xin Jiang; Jef K De Brabander
Journal:  J Am Chem Soc       Date:  2012-10-04       Impact factor: 15.419

7.  Total synthesis of irciniastatin A (Psymberin).

Authors:  Michael T Crimmins; Jason M Stevens; Gregory M Schaaf
Journal:  Org Lett       Date:  2009-09-03       Impact factor: 6.005

8.  Design, Synthesis, and Evaluation of Irciniastatin Analogues: Simplification of the Tetrahydropyran Core and the C(11) Substituents.

Authors:  Qi Liu; Chihui An; Karen TenDyke; Hongsheng Cheng; Young Yongchun Shen; Adam T Hoye; Amos B Smith
Journal:  J Org Chem       Date:  2016-02-16       Impact factor: 4.354
  8 in total

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