Literature DB >> 20161322

An approach to the synthesis of dimeric resveratrol natural products via a palladium-catalyzed domino reaction.

Jenna L Jeffrey1, Richmond Sarpong.   

Abstract

A route for the rapid assembly of the carbon framework of several resveratrol natural products is presented. A palladium-catalyzed domino reaction of bromostilbene derivative 6 and tolane 7, involving two sequential Heck coupling reactions, provides access to the benzofulvene-based core of various resveratrol-derived natural products. The carbon skeleton of pallidol and its congeners is achieved by a Lewis acid-induced Nazarov-type oxidative cyclization of 9.

Entities:  

Year:  2009        PMID： 20161322      PMCID： PMC2678734          DOI： 10.1016/j.tetlet.2009.02.067

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


  11 in total

1.  Domino Reactions in Organic Synthesis.

Authors:  Lutz F. Tietze
Journal:  Chem Rev       Date:  1996-02-01       Impact factor: 60.622

2.  Total synthesis of (+/-)-quadrangularin A.

Authors:  Wenling Li; Hao Li; Ying Li; Zijie Hou
Journal:  Angew Chem Int Ed Engl       Date:  2006-11-20       Impact factor: 15.336

3.  Cytotoxic properties of oligostilbenoids from the tree barks of Hopea dryobalanoides.

Authors:  Euis H Hakim; Lia D Juliawaty; Yana M Syah; Laily bin Din; Emilio L Ghisalberti; Jalifah Latip; Ikram M Said; Sjamsul A Achmad
Journal:  Z Naturforsch C J Biosci       Date:  2005 Sep-Oct

4.  Total synthesis of resveratrol-based natural products: a chemoselective solution.

Authors:  Scott A Snyder; Alexandros L Zografos; Yunqing Lin
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

5.  Total synthesis of diverse carbogenic complexity within the resveratrol class from a common building block.

Authors:  Scott A Snyder; Steven P Breazzano; Audrey G Ross; Yunqing Lin; Alexandros L Zografos
Journal:  J Am Chem Soc       Date:  2009-02-11       Impact factor: 15.419

6.  Oligostilbenoids in stem bark of Vatica rassak.

Authors:  T Tanaka; T Ito; K Nakaya; M Iinuma; S Riswan
Journal:  Phytochemistry       Date:  2000-05       Impact factor: 4.072

7.  Cancer chemopreventive activity of resveratrol, a natural product derived from grapes.

Authors:  M Jang; L Cai; G O Udeani; K V Slowing; C F Thomas; C W Beecher; H H Fong; N R Farnsworth; A D Kinghorn; R G Mehta; R C Moon; J M Pezzuto
Journal:  Science       Date:  1997-01-10       Impact factor: 47.728

8.  Synthesis and biological evaluation of boronic acid containing cis-stilbenes as apoptotic tubulin polymerization inhibitors.

Authors:  Hiroyuki Nakamura; Hirokazu Kuroda; Hiroyuki Saito; Ryo Suzuki; Takao Yamori; Kazuo Maruyama; Tatsuya Haga
Journal:  ChemMedChem       Date:  2006-07       Impact factor: 3.466

9.  Phloroglucinol derivatives from Mallotus pallidus.

Authors:  Butsarakham Supudompol; Kittisak Likhitwitayawuid; Peter J Houghton
Journal:  Phytochemistry       Date:  2004-09       Impact factor: 4.072

10.  Resveratrol prolongs lifespan and retards the onset of age-related markers in a short-lived vertebrate.

Authors:  Dario R Valenzano; Eva Terzibasi; Tyrone Genade; Antonino Cattaneo; Luciano Domenici; Alessandro Cellerino
Journal:  Curr Biol       Date:  2006-02-07       Impact factor: 10.834
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  6 in total

Review 1.  Chemistry and Biology of Resveratrol-Derived Natural Products.

Authors:  Mitchell H Keylor; Bryan S Matsuura; Corey R J Stephenson
Journal:  Chem Rev       Date:  2015-04-02       Impact factor: 60.622

2.  Structural revision and total synthesis of caraphenol B and C.

Authors:  Scott A Snyder; Zachary G Brill
Journal:  Org Lett       Date:  2011-09-26       Impact factor: 6.005

3.  Total syntheses of hopeanol and hopeahainol A empowered by a chiral Brønsted acid induced pinacol rearrangement.

Authors:  Scott A Snyder; Stephen B Thomas; Agathe C Mayer; Steven P Breazzano
Journal:  Angew Chem Int Ed Engl       Date:  2012-03-16       Impact factor: 15.336

4.  A scalable biomimetic synthesis of resveratrol dimers and systematic evaluation of their antioxidant activities.

Authors:  Bryan S Matsuura; Mitchell H Keylor; Bo Li; YuXuan Lin; Shelby Allison; Derek A Pratt; Corey R J Stephenson
Journal:  Angew Chem Int Ed Engl       Date:  2015-02-04       Impact factor: 15.336

5.  Electrochemically Mediated Oxidation of Sensitive Propargylic Benzylic Alcohols.

Authors:  Chad E Hatch; Maxwell I Martin; Philip H Gilmartin; Lu Xiong; Danielle J Beam; Glenn P A Yap; Matthew J Von Bargen; Joel Rosenthal; William J Chain
Journal:  Org Lett       Date:  2022-02-11       Impact factor: 6.072

6.  Concise synthesis of pauciflorol F using a Larock annulation.

Authors:  Jenna L Jeffrey; Richmond Sarpong
Journal:  Org Lett       Date:  2009-12-03       Impact factor: 6.005
  6 in total

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