Literature DB >> 20161637

Synthesis of (+/-)-Oleocanthal via a Tandem Intramolecular Michael Cyclization-HWE Olefination.

Brandon J English1, Robert M Williams.   

Abstract

A synthesis of racemic oleocanthal has been accomplished in eleven steps from 1,3 propanediol by a key tandem intramolecular Michael cyclization-Horner Wadsworth Emmons olefination.

Entities:  

Year:  2009        PMID： 20161637      PMCID： PMC2817976          DOI： 10.1016/j.tetlet.2009.03.145

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  16 in total

1.  Synthesis and assignment of absolute configuration of (-)-oleocanthal: a potent, naturally occurring non-steroidal anti-inflammatory and anti-oxidant agent derived from extra virgin olive oils.

Authors:  Amos B Smith; Qiang Han; Paul A S Breslin; Gary K Beauchamp
Journal:  Org Lett       Date:  2005-10-27       Impact factor: 6.005

2.  The telescoped intramolecular michael/olefination (TIMO) approach to alpha-alkylidene-gamma-butyrolactones: synthesis of (+)-paeonilactone B.

Authors:  Michael G Edwards; Martin N Kenworthy; Russell R A Kitson; Mark S Scott; Richard J K Taylor
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

3.  New iridoids from the medicinal plant Barleria prionitis with potent activity against respiratory syncytial virus.

Authors:  J L Chen; P Blanc; C A Stoddart; M Bogan; E J Rozhon; N Parkinson; Z Ye; R Cooper; M Balick; W Nanakorn; M R Kernan
Journal:  J Nat Prod       Date:  1998-10       Impact factor: 4.050

4.  Antiviral activity of seven iridoids, three saikosaponins and one phenylpropanoid glycoside extracted from Bupleurum rigidum and Scrophularia scorodonia.

Authors:  Paulina Bermejo; María José Abad; Ana María Díaz; Lidia Fernández; Javier De Santos; Sandra Sanchez; Lucinda Villaescusa; Luis Carrasco; Alicia Irurzun
Journal:  Planta Med       Date:  2002-02       Impact factor: 3.352

5.  Effects of some iridoids from plant origin on arachidonic acid metabolism in cellular systems.

Authors:  P Bermejo Benito; A M Díaz Lanza; A M Silván Sen; J De Santos Galindez; L Fernandez Matellano; A Sanz Gómez; M J Abad Martínez
Journal:  Planta Med       Date:  2000-05       Impact factor: 3.352

6.  New and known iridoid- and phenylethanoid glycosides from Harpagophytum procumbens and their in vitro inhibition of human leukocyte elastase.

Authors:  Kerstin Boje; Matthias Lechtenberg; Adolf Nahrstedt
Journal:  Planta Med       Date:  2003-09       Impact factor: 3.352

7.  Iridoid glucosides from the flowers of Barleria lupulina.

Authors:  Sunit Suksamrarn; Kanjana Wongkrajang; Kanyawim Kirtikara; Apichart Suksamrarn
Journal:  Planta Med       Date:  2003-09       Impact factor: 3.352

8.  Complement-inhibiting iridoids from Morinda morindoides.

Authors:  Kanyanga Cimanga; Nina Hermans; Sandra Apers; Sabine Van Miert; Hilde Van den Heuvel; Magda Claeys; Luc Pieters; Arnold Vlietinck
Journal:  J Nat Prod       Date:  2003-01       Impact factor: 4.050

9.  Inhibitory effects of a new iridoid, patridoid II and its isomers, on nitric oxide and TNF-alpha production in cultured murine macrophages.

Authors:  Hye Kyung Ju; Tae Chul Moon; Eunkyung Lee; Suk-Hwan Baek; Ren-Bo An; KiHwan Bae; Kun Ho Son; Hyun Pyo Kim; Sam Sik Kang; Sung Ho Lee; Jong Keun Son; Hyeun Wook Chang
Journal:  Planta Med       Date:  2003-10       Impact factor: 3.352

10.  Absolute stereostructures of hydramacrosides A and B, new bioactive secoiridoid glucoside complexes from the leaves of Hydrangea macrophylla Seringe var. thunbergii Makino.

Authors:  M Yoshikawa; T Ueda; H Matsuda; J Yamahara; N Murakami
Journal:  Chem Pharm Bull (Tokyo)       Date:  1994-08       Impact factor: 1.645
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  4 in total

1.  A divergent strategy for the synthesis of secologanin derived natural products.

Authors:  Brandon J English; Robert M Williams
Journal:  J Org Chem       Date:  2010-10-22       Impact factor: 4.354

Review 2.  The Biological Activities of Oleocanthal from a Molecular Perspective.

Authors:  Kok-Lun Pang; Kok-Yong Chin
Journal:  Nutrients       Date:  2018-05-06       Impact factor: 5.717

Review 3.  Potential Uses of Olive Oil Secoiridoids for the Prevention and Treatment of Cancer: A Narrative Review of Preclinical Studies.

Authors:  Maria Rita Emma; Giuseppa Augello; Vita Di Stefano; Antonina Azzolina; Lydia Giannitrapani; Giuseppe Montalto; Melchiorre Cervello; Antonella Cusimano
Journal:  Int J Mol Sci       Date:  2021-01-27       Impact factor: 5.923

4.  Natural Deep Eutectic Solvent as Extraction Media for the Main Phenolic Compounds from Olive Oil Processing Wastes.

Authors:  Sonia Bonacci; Maria Luisa Di Gioia; Paola Costanzo; Loredana Maiuolo; Sofia Tallarico; Monica Nardi
Journal:  Antioxidants (Basel)       Date:  2020-06-11
  4 in total

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