Literature DB >> 20849144

Formal total synthesis of okadaic acid via regiocontrolled gold(I)-catalyzed spiroketalizations.

Chao Fang1, Yucheng Pang, Craig J Forsyth.   

Abstract

Both C19 and C34 spiroketal domains of okadaic acid were assembled using gold(I) chloride catalyzed spiroketalizations, and the two resulting fragments were coupled to give the C15-C38 fragment of okadaic acid, a known intermediate for the total synthesis of this important natural product.

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Year:  2010        PMID: 20849144     DOI: 10.1021/ol101833h

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


  7 in total

1.  Spirastrellolide E: Synthesis of an advanced C(1)-C(24) southern hemisphere.

Authors:  Alexander Sokolsky; Xiaozhao Wang; Amos B Smith
Journal:  Tetrahedron Lett       Date:  2015-06-03       Impact factor: 2.415

2.  Leveraging the micellar effect: gold-catalyzed dehydrative cyclizations in water at room temperature.

Authors:  Stefan R K Minkler; Nicholas A Isley; Daniel J Lippincott; Norbert Krause; Bruce H Lipshutz
Journal:  Org Lett       Date:  2014-01-16       Impact factor: 6.005

3.  A gold-catalyzed alkyne-diol cycloisomerization for the synthesis of oxygenated 5,5-spiroketals.

Authors:  Sami F Tlais; Gregory B Dudley
Journal:  Beilstein J Org Chem       Date:  2011-05-04       Impact factor: 2.883

4.  When gold can do what iodine cannot do: A critical comparison.

Authors:  Sara Hummel; Stefan F Kirsch
Journal:  Beilstein J Org Chem       Date:  2011-06-22       Impact factor: 2.883

5.  Gold(I)-Catalyzed Activation of Alkynes for the Construction of Molecular Complexity.

Authors:  Ruth Dorel; Antonio M Echavarren
Journal:  Chem Rev       Date:  2015-04-06       Impact factor: 60.622

6.  Gold-catalyzed glycosidation for the synthesis of trisaccharides by applying the armed-disarmed strategy.

Authors:  Abhijeet K Kayastha; Srinivas Hotha
Journal:  Beilstein J Org Chem       Date:  2013-10-18       Impact factor: 2.883

Review 7.  Gold-catalyzed cyclizations of alkynol-based compounds: synthesis of natural products and derivatives.

Authors:  Benito Alcaide; Pedro Almendros; José M Alonso
Journal:  Molecules       Date:  2011-09-13       Impact factor: 4.411

  7 in total

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