Literature DB >> 19572569

Progress toward the total synthesis of psymberin/irciniastatin A.

Lauren E Brown1, Yakira R Landaverry, James R Davies, Kristin A Milinkevich, Sandra Ast, Joseph S Carlson, Allen G Oliver, Joseph P Konopelski.   

Abstract

In this paper, we describe our synthesis of four key building blocks for the total synthesis of psymberin (1) and its C4 epimer (2). Despite early difficulties in processing material to the advanced intermediate stage, we have been successful in developing high-yielding syntheses for the pyran core, natural side chain, 4-epi side chain, and aryl fragments of the molecule. Our findings from the optimization process are presented herein.

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Year:  2009        PMID： 19572569      PMCID： PMC2736341          DOI： 10.1021/jo9009003

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  19 in total

1.  Absolute structure and absolute configuration.

Authors: 
Journal:  Acta Crystallogr A       Date:  1999-09-01       Impact factor: 2.290

2.  IBX-mediated oxidation of primary alcohols and aldehydes to form carboxylic acids.

Authors:  Ralph Mazitschek; Marcel Mülbaier; Athanassios Giannis
Journal:  Angew Chem Int Ed Engl       Date:  2002-11-04       Impact factor: 15.336

3.  Antineoplastic agents. 520. Isolation and structure of irciniastatins A and B from the Indo-Pacific marine sponge Ircinia ramosa.

Authors:  George R Pettit; Jun-Ping Xu; Jean-Charles Chapuis; Robin K Pettit; Larry P Tackett; Dennis L Doubek; John N A Hooper; Jean M Schmidt
Journal:  J Med Chem       Date:  2004-02-26       Impact factor: 7.446

4.  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

5.  The discovery of potent antitumor agent C11-deoxypsymberin/irciniastatin A: total synthesis and biology of advanced psymberin analogs.

Authors:  Xianhai Huang; Ning Shao; Robert Huryk; Anandan Palani; Robert Aslanian; Cynthia Seidel-Dugan
Journal:  Org Lett       Date:  2009-02-19       Impact factor: 6.005

6.  Stereochemical assignment of the C1-C6 fragment of psymberin by synthesis and natural product degradation.

Authors:  Michael E Green; Jason C Rech; Paul E Floreancig
Journal:  Org Lett       Date:  2005-09-15       Impact factor: 6.005

7.  Anti-AIDS agents. 37. Synthesis and structure-activity relationships of (3'R,4'R)-(+)-cis-khellactone derivatives as novel potent anti-HIV agents.

Authors:  L Xie; Y Takeuchi; L M Cosentino; K H Lee
Journal:  J Med Chem       Date:  1999-07-15       Impact factor: 7.446

8.  A formal synthesis of psymberin.

Authors:  Ning Shangguan; Sezgin Kiren; Lawrence J Williams
Journal:  Org Lett       Date:  2007-02-24       Impact factor: 6.005

9.  Catalytic asymmetric addition of alcohols to imines: enantioselective preparation of chiral N,O-aminals.

Authors:  Guilong Li; Frank R Fronczek; Jon C Antilla
Journal:  J Am Chem Soc       Date:  2008-08-23       Impact factor: 15.419

10.  The total synthesis of psymberin.

Authors:  Xianhai Huang; Ning Shao; Anandan Palani; Robert Aslanian; Alexei Buevich
Journal:  Org Lett       Date:  2007-05-25       Impact factor: 6.005
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  4 in total

1.  Total synthesis of the cyanolide A aglycon.

Authors:  Michael R Gesinski; Scott D Rychnovsky
Journal:  J Am Chem Soc       Date:  2011-06-08       Impact factor: 15.419

Review 2.  Transition Metal Catalysis Controlled by Hydrogen Bonding in the Second Coordination Sphere.

Authors:  Joost N H Reek; Bas de Bruin; Sonja Pullen; Tiddo J Mooibroek; Alexander M Kluwer; Xavier Caumes
Journal:  Chem Rev       Date:  2022-05-20       Impact factor: 72.087

3.  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

4.  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
  4 in total

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