Literature DB >> 11893183

Regioselective synthesis of the bridged tricyclic core of Garcinia natural products via intramolecular aryl acrylate cycloadditions.

Eric J Tisdale1, Chinmay Chowdhury, Binh G Vong, Hongmei Li, Emmanuel A Theodorakis.   

Abstract

[reaction: see text] Two different routes to the tricyclic core of Garcinia-derived natural products are described. The first approach is based on a tandem Claisen/Diels-Alder rearrangement and delivers the desired lactone 14. The second approach, employing a Wessely oxidation/Diels-Alder protocol, leads to the same caged heterocycle, albeit with modified constitution.

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Year:  2002        PMID： 11893183     DOI： 10.1021/ol017278w

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


  8 in total

1.  Unified synthesis of caged Garcinia natural products based on a site-selective Claisen/Diels-Alder/Claisen rearrangement.

Authors:  Eric J Tisdale; Irina Slobodov; Emmanuel A Theodorakis
Journal:  Proc Natl Acad Sci U S A       Date:  2004-06-21       Impact factor: 11.205

Review 2.  Chemistry and biology of the caged Garcinia xanthones.

Authors:  Oraphin Chantarasriwong; Ayse Batova; Warinthorn Chavasiri; Emmanuel A Theodorakis
Journal:  Chemistry       Date:  2010-09-03       Impact factor: 5.236

3.  Subcellular localization and activity of gambogic acid.

Authors:  Gianni Guizzunti; Ayse Batova; Oraphin Chantarasriwong; Marianna Dakanali; Emmanuel A Theodorakis
Journal:  Chembiochem       Date:  2012-04-24       Impact factor: 3.164

4.  The Domino Way to Heterocycles.

Authors:  Albert Padwa; Scott K Bur
Journal:  Tetrahedron       Date:  2007-06-18       Impact factor: 2.457

Review 5.  Neurotrophic natural products: chemistry and biology.

Authors:  Jing Xu; Michelle H Lacoske; Emmanuel A Theodorakis
Journal:  Angew Chem Int Ed Engl       Date:  2013-12-18       Impact factor: 15.336

Review 6.  Dearomatization strategies in the synthesis of complex natural products.

Authors:  Stéphane P Roche; John A Porco
Journal:  Angew Chem Int Ed Engl       Date:  2011-04-19       Impact factor: 15.336

7.  Evaluation of the pharmacophoric motif of the caged Garcinia xanthones.

Authors:  Oraphin Chantarasriwong; Woo Cheal Cho; Ayse Batova; Warinthorn Chavasiri; Curtis Moore; Arnold L Rheingold; Emmanuel A Theodorakis
Journal:  Org Biomol Chem       Date:  2009-09-24       Impact factor: 3.876

8.  A-ring oxygenation modulates the chemistry and bioactivity of caged Garcinia xanthones.

Authors:  Kristyna M Elbel; Gianni Guizzunti; Maria A Theodoraki; Jing Xu; Ayse Batova; Marianna Dakanali; Emmanuel A Theodorakis
Journal:  Org Biomol Chem       Date:  2013-05-28       Impact factor: 3.876
  8 in total

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