Literature DB >> 19902905

Concise synthesis of pauciflorol F using a Larock annulation.

Jenna L Jeffrey1, Richmond Sarpong.   

Abstract

A Pd-catalyzed Larock annulation provides expedient access to a subset of resveratrol-derived natural products. The reported approach resulted in the structural revision of an intermediate en route to the natural product pauciflorol F, the total synthesis of which proceeded in two steps from the requisite pentannulation product.

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Year:  2009        PMID： 19902905      PMCID： PMC2787984          DOI： 10.1021/ol902141z

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


  12 in total

1.  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

2.  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

3.  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

4.  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

5.  Nucleophilic acylation of o-quinone methides: an umpolung strategy for the synthesis of alpha-aryl ketones and benzofurans.

Authors:  Anita E Mattson; Karl A Scheidt
Journal:  J Am Chem Soc       Date:  2007-03-23       Impact factor: 15.419

6.  Plasma, urine and tissue levels of trans- and cis-resveratrol (3,4',5-trihydroxystilbene) after short-term or prolonged administration of red wine to rats.

Authors:  A A Bertelli; L Giovannini; R Stradi; A Bertelli; J P Tillement
Journal:  Int J Tissue React       Date:  1996

7.  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

8.  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

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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  15 in total

Review 1.  Constructing molecular complexity and diversity: total synthesis of natural products of biological and medicinal importance.

Authors:  K C Nicolaou; Christopher R H Hale; Christian Nilewski; Heraklidia A Ioannidou
Journal:  Chem Soc Rev       Date:  2012-06-28       Impact factor: 54.564

Review 2.  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

3.  Electrochemical Dimerization of Phenylpropenoids and the Surprising Antioxidant Activity of the Resultant Quinone Methide Dimers.

Authors:  Kevin J Romero; Matthew S Galliher; Mark A R Raycroft; Jean-Philippe R Chauvin; Irene Bosque; Derek A Pratt; Corey R J Stephenson
Journal:  Angew Chem Int Ed Engl       Date:  2018-11-26       Impact factor: 15.336

4.  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

5.  Harnessing quinone methides: total synthesis of (±)-vaticanol A.

Authors:  Tue H Jepsen; Stephen B Thomas; Yunqing Lin; Christos I Stathakis; Irene de Miguel; Scott A Snyder
Journal:  Angew Chem Int Ed Engl       Date:  2014-05-19       Impact factor: 15.336

6.  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

7.  A flow-microreactor approach to protecting-group-free synthesis using organolithium compounds.

Authors:  Heejin Kim; Aiichiro Nagaki; Jun-ichi Yoshida
Journal:  Nat Commun       Date:  2011       Impact factor: 14.919

8.  Palladium/Norbornene-Catalyzed Indenone Synthesis from Simple Aryl Iodides: Concise Syntheses of Pauciflorol F and Acredinone A.

Authors:  Feipeng Liu; Zhe Dong; Jianchun Wang; Guangbin Dong
Journal:  Angew Chem Int Ed Engl       Date:  2019-01-16       Impact factor: 15.336

9.  Synthesis of resveratrol tetramers via a stereoconvergent radical equilibrium.

Authors:  Mitchell H Keylor; Bryan S Matsuura; Markus Griesser; Jean-Philippe R Chauvin; Ryan A Harding; Mariia S Kirillova; Xu Zhu; Oliver J Fischer; Derek A Pratt; Corey R J Stephenson
Journal:  Science       Date:  2016-12-09       Impact factor: 47.728

10.  Synthesis of Vitisins A and D Enabled by a Persistent Radical Equilibrium.

Authors:  Kevin J Romero; Mitchell H Keylor; Markus Griesser; Xu Zhu; Ethan J Strobel; Derek A Pratt; Corey R J Stephenson
Journal:  J Am Chem Soc       Date:  2020-03-24       Impact factor: 15.419
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