Literature DB >> 17217291

Synthesis of 2-epi-amphidinolide E: an unexpected and highly selective C(2)inversion during an esterification reaction.

Porino Va1, William R Roush.   

Abstract

A synthesis of 2-epi-amphidinolide E (1) has been accomplished via an unexpected and highly diastereoselective C(2) stereochemical inversion during the modified Yamaguchi esterification of alcohol 4b and Fe(CO)3-complexed dienoic acid 7. [reaction: see text].

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Year:  2007        PMID： 17217291      PMCID： PMC2593877          DOI： 10.1021/ol0628098

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


  32 in total

1.  Facile acylation of sterically hindered alcohols through ketene intermediates.

Authors:  M Nahmany; A Melman
Journal:  Org Lett       Date:  2001-11-15       Impact factor: 6.005

2.  Olefin Metathesis and Beyond A list of abbreviations can be found at the end of this article.

Authors: 
Journal:  Angew Chem Int Ed Engl       Date:  2000-09-01       Impact factor: 15.336

3.  Total synthesis of proposed amphidinolide A via a highly selective ring-closing metathesis.

Authors:  Robert E Maleczka; Lamont R Terrell; Feng Geng; Joseph S Ward
Journal:  Org Lett       Date:  2002-08-22       Impact factor: 6.005

4.  Total synthesis of (-)-amphidinolide E.

Authors:  Chan Hyuk Kim; Hyo Jung An; Won Kyo Shin; Wei Yu; Sang Kook Woo; Soon Kyu Jung; Eun Lee
Journal:  Angew Chem Int Ed Engl       Date:  2006-12-04       Impact factor: 15.336

5.  Total synthesis and revision of C6 stereochemistry of (+)-amphidinolide W.

Authors:  Arun K Ghosh; Gangli Gong
Journal:  J Org Chem       Date:  2006-02-03       Impact factor: 4.354

6.  Total synthesis of (+)-amphidinolide A. Assembly of the fragments.

Authors:  Barry M Trost; Stephen T Wrobleski; John D Chisholm; Paul E Harrington; Michael Jung
Journal:  J Am Chem Soc       Date:  2005-10-05       Impact factor: 15.419

7.  Synthesis of the C6-C21 segment of amphidinolide E.

Authors:  James A Marshall; Gregory Schaaf; Andrew Nolting
Journal:  Org Lett       Date:  2005-11-10       Impact factor: 6.005

8.  Alkene-alkyne coupling as a linchpin: an efficient and convergent synthesis of amphidinolide P.

Authors:  Barry M Trost; Julien P N Papillon
Journal:  J Am Chem Soc       Date:  2004-10-27       Impact factor: 15.419

9.  Total synthesis of amphidinolide E.

Authors:  Porino Va; William R Roush
Journal:  J Am Chem Soc       Date:  2006-12-20       Impact factor: 15.419

10.  Enantioselective total synthesis of (+)-amphidinolide t1.

Authors:  Arun K Ghosh; Chunfeng Liu
Journal:  J Am Chem Soc       Date:  2003-03-05       Impact factor: 15.419
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  3 in total

1.  Recent Applications of Acyclic (Diene)iron Complexes and (Dienyl)iron Cations in Organic Synthesis.

Authors:  William A Donaldson; Subhabrata Chaudhury
Journal:  European J Org Chem       Date:  2009-08

2.  Total Synthesis of Amphidinolide E and Amphidinolide E Stereoisomers.

Authors:  Porino Va; William R Roush
Journal:  Tetrahedron       Date:  2007-06-25       Impact factor: 2.457

Review 3.  The Tetrahydrofuran Motif in Polyketide Marine Drugs.

Authors:  Laura Fernández-Peña; Carlos Díez-Poza; Paula González-Andrés; Asunción Barbero
Journal:  Mar Drugs       Date:  2022-02-03       Impact factor: 5.118
  3 in total

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