Literature DB >> 16774259

Synthesis of precursors of the agalacto (exo) fragment of the quartromicins via an auxiliary-controlled exo-selective Diels-Alder reaction.

Jun Qi1, William R Roush.   

Abstract

[reaction: see text] A direct synthesis of the alpha-hydroxyaldehyde exo-5, a precursor of the exo-spirotetronate subunit of the quartromicins, was achieved through an exo-selective Lewis acid-catalyzed Diels-Alder reaction of dienophile 12a and diene 1.

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Year:  2006        PMID： 16774259      PMCID： PMC2515626          DOI： 10.1021/ol0609208

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


  5 in total

1.  Partial stereochemical assignment of quartromicins A3 and D3.

Authors:  William R Roush; David A Barda
Journal:  Org Lett       Date:  2002-05-02       Impact factor: 6.005

2.  Studies on the synthesis of quartromicins a(3) and d(3): synthesis of the vertical and horizontal bis-spirotetronate fragments.

Authors:  Tony K Trullinger; Jun Qi; William R Roush
Journal:  J Org Chem       Date:  2006-09-01       Impact factor: 4.354

3.  Azide and Cyanide Displacements via Hypervalent Silicate Intermediates.

Authors:  Eric D. Soli; Amy S. Manoso; Michael C. Patterson; Philip DeShong; David A. Favor; Ralph Hirschmann; Amos B. Smith
Journal:  J Org Chem       Date:  1999-04-30       Impact factor: 4.354

4.  Diastereoselective synthesis of the endo- and exo-spirotetronate subunits of the quartromicins. The first enantioselective Diels-Alder reaction of an acyclic (Z)-1,3-diene.

Authors:  William R Roush; Chris Limberakis; Roxanne K Kunz; David A Barda
Journal:  Org Lett       Date:  2002-05-02       Impact factor: 6.005

5.  Quartromicin, a complex of novel antiviral antibiotics. I. Production, isolation, physico-chemical properties and antiviral activity.

Authors:  M Tsunakawa; O Tenmyo; K Tomita; N Naruse; C Kotake; T Miyaki; M Konishi; T Oki
Journal:  J Antibiot (Tokyo)       Date:  1992-02       Impact factor: 2.649
  5 in total
  5 in total

1.  Selective synthesis of 3-hydroxy acids from Meldrum's acids using SmI2-H2O.

Authors:  Michal Szostak; Malcolm Spain; David J Procter
Journal:  Nat Protoc       Date:  2012-04-26       Impact factor: 13.491

2.  Studies on the synthesis of quartromicins a(3) and d(3): synthesis of the vertical and horizontal bis-spirotetronate fragments.

Authors:  Tony K Trullinger; Jun Qi; William R Roush
Journal:  J Org Chem       Date:  2006-09-01       Impact factor: 4.354

3.  Diels-Alder exo selectivity in terminal-substituted dienes and dienophiles: experimental discoveries and computational explanations.

Authors:  Yu-hong Lam; Paul Ha-Yeon Cheong; José M Blasco Mata; Steven J Stanway; Véronique Gouverneur; K N Houk
Journal:  J Am Chem Soc       Date:  2009-02-11       Impact factor: 15.419

4.  Unconventional exo selectivity in thermal normal-electron-demand Diels-Alder reactions.

Authors:  Guo-Ming Ho; Ci-Jhang Huang; Elise Yu-Tzu Li; Sheng-Kai Hsu; Ti Wu; Medel Manuel L Zulueta; Kevin Binchia Wu; Shang-Cheng Hung
Journal:  Sci Rep       Date:  2016-10-12       Impact factor: 4.379

5.  Molecular design principles towards exo-exclusive Diels-Alder reactions.

Authors:  Ci-Jhang Huang; Elise Y Li
Journal:  RSC Adv       Date:  2019-03-04       Impact factor: 3.361
  5 in total

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