Literature DB >> 14727628

Biomimetic total synthesis of forbesione and desoxymorellin utilizing a tandem Claisen/Diels--Alder/Claisen rearrangement.

Eric J Tisdale1, Irina Slobodov, Emmanuel A Theodorakis.   

Abstract

A concise synthesis of forbesione (1) and desoxymorellin (3) is presented. Central to the strategy is a biomimetic Claisen/Diels-Alder/Claisen reaction cascade that proceeds in a regioselective manner and produces the desired scaffold exclusively. The observed regioselectivity and product distribution of the Claisen/Diels-Alder/Claisen reaction are attributed to the electronic effects of the xanthone oxygen (O10), the C9 carbonyl group and the nature of the C1 functionality.

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Year:  2003        PMID： 14727628     DOI： 10.1039/b311833a

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN： 1477-0520            Impact factor:   3.876


  15 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

Review 4.  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

5.  Caged Garcinia Xanthones, a Novel Chemical Scaffold with Potent Antimalarial Activity.

Authors:  Hangjun Ke; Joanne M Morrisey; Shiwei Qu; Oraphin Chantarasriwong; Michael W Mather; Emmanuel A Theodorakis; Akhil B Vaidya
Journal:  Antimicrob Agents Chemother       Date:  2016-12-27       Impact factor: 5.191

6.  Enzymatic basis of ribosomal peptide prenylation in cyanobacteria.

Authors:  John A McIntosh; Mohamed S Donia; Satish K Nair; Eric W Schmidt
Journal:  J Am Chem Soc       Date:  2011-08-04       Impact factor: 15.419

Review 7.  Toward a symphony of reactivity: cascades involving catalysis and sigmatropic rearrangements.

Authors:  Amanda C Jones; Jeremy A May; Richmond Sarpong; Brian M Stoltz
Journal:  Angew Chem Int Ed Engl       Date:  2014-03-03       Impact factor: 15.336

8.  Formal synthesis of (-)-englerin A and cytotoxicity studies of truncated englerins.

Authors:  Jing Xu; Eduardo J E Caro-Diaz; Ayse Batova; Steven D E Sullivan; Emmanuel A Theodorakis
Journal:  Chem Asian J       Date:  2012-03-13

9.  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

10.  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
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