Literature DB >> 12713306

Regioselective synthesis of the tricyclic core of lateriflorone.

Eric J Tisdale1, Hongmei Li, Binh G Vong, Sun Hee Kim, Emmanuel A Theodorakis.   

Abstract

An efficient synthetic approach to the tricyclic core 8 of lateriflorone is described. Essential to the synthesis was the implementation of a biomimetic tandem Claisen/Diels-Alder reaction that produced the desired tricyclic scaffold as a single isomer. A rationalization of the excellent regio and stereoselectivity of this transformation is also proposed. [reaction: see text]

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Year:  2003        PMID: 12713306     DOI: 10.1021/ol034276y

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


  5 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.  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

4.  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

5.  Discovery and evaluation of novel inhibitors of mycobacterium protein tyrosine phosphatase B from the 6-Hydroxy-benzofuran-5-carboxylic acid scaffold.

Authors:  Yantao He; Jie Xu; Zhi-Hong Yu; Andrea M Gunawan; Li Wu; Lina Wang; Zhong-Yin Zhang
Journal:  J Med Chem       Date:  2013-01-25       Impact factor: 7.446

  5 in total

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