Literature DB >> 21942557

Structural revision and total synthesis of caraphenol B and C.

Scott A Snyder1, Zachary G Brill.   

Abstract

Chemical syntheses of two stereochemically unique resveratrol dimers, caraphenols B and C, have shown that their structures are misassigned. Thoughts on their potential chemical etiology led to an alternate structural proposal that has been confirmed through synthesis, one indicating that the substituents on their respective indane systems exist in a relative trans,trans orientation rather than the originally postulated all-cis arrangement.
© 2011 American Chemical Society

Entities:  

Mesh：

Substances：

Year:  2011        PMID： 21942557      PMCID： PMC3224822          DOI： 10.1021/ol2022406

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


  18 in total

1.  Regioselective oxidative coupling of 4-hydroxystilbenes: synthesis of resveratrol and epsilon-viniferin (E)-dehydrodimers.

Authors:  Magoichi Sako; Hiroyuki Hosokawa; Tetsuro Ito; Munekazu Iinuma
Journal:  J Org Chem       Date:  2004-04-02       Impact factor: 4.354

2.  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

3.  Total synthesis of hopeahainol A and hopeanol.

Authors:  K C Nicolaou; T Robert Wu; Qiang Kang; David Y-K Chen
Journal:  Angew Chem Int Ed Engl       Date:  2009       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.  Two new antioxidant stilbene dimers, parthenostilbenins A and B from Parthenocissus tricuspidata.

Authors:  Hyoung Ja Kim; Muhammad Saleem; Seon Hee Seo; Changbae Jin; Yong Sup Lee
Journal:  Planta Med       Date:  2005-10       Impact factor: 3.352

6.  Total syntheses of heimiol A, hopeahainol D, and constrained analogues.

Authors:  Scott A Snyder; Nathan E Wright; Jason J Pflueger; Steven P Breazzano
Journal:  Angew Chem Int Ed Engl       Date:  2011-07-26       Impact factor: 15.336

7.  Regio- and stereoselective biomimetic synthesis of oligostilbenoid dimers from resveratrol analogues: influence of the solvent, oxidant, and substitution.

Authors:  Saraswati S Velu; Irmaizatussyehdany Buniyamin; Lee Kiew Ching; Fareeda Feroz; Ibrahim Noorbatcha; Lim Chuan Gee; Khalijah Awang; Ibtisam Abd Wahab; Jean-Frédéric Faizal Weber
Journal:  Chemistry       Date:  2008       Impact factor: 5.236

8.  Regioselective reactions for programmable resveratrol oligomer synthesis.

Authors:  Scott A Snyder; Andreas Gollner; Maria I Chiriac
Journal:  Nature       Date:  2011-06-22       Impact factor: 49.962

9.  Modular synthesis of polyphenolic benzofurans, and application in the total synthesis of malibatol a and shoreaphenol.

Authors:  David Y-K Chen; Qiang Kang; T Robert Wu
Journal:  Molecules       Date:  2010-08-27       Impact factor: 4.411

10.  Sirtuin activators mimic caloric restriction and delay ageing in metazoans.

Authors:  Jason G Wood; Blanka Rogina; Siva Lavu; Konrad Howitz; Stephen L Helfand; Marc Tatar; David Sinclair
Journal:  Nature       Date:  2004-07-14       Impact factor: 69.504
View more
  10 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.  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

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.  9-Membered carbocycle formation: development of distinct Friedel-Crafts cyclizations and application to a scalable total synthesis of (±)-caraphenol A.

Authors:  Nathan E Wright; Scott A Snyder
Journal:  Angew Chem Int Ed Engl       Date:  2014-03-24       Impact factor: 15.336

5.  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

6.  Ruthenium(0)-Catalyzed [4+2] Cycloaddition of Acetylenic Aldehydes with α-Ketols: Convergent Construction of Angucycline Ring Systems.

Authors:  Aakarsh Saxena; Felix Perez; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2015-12-09       Impact factor: 15.336

7.  2,4-Dibromo-2,3-dihydro-1H-inden-1-yl acetate.

Authors:  Ismail Celik; Mehmet Akkurt; Makbule Yilmaz; Ahmet Tutar; Ramazan Erenler; Canan Kazak
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-05-26

8.  A strategy for complex dimer formation when biomimicry fails: total synthesis of ten coccinellid alkaloids.

Authors:  Trevor C Sherwood; Adam H Trotta; Scott A Snyder
Journal:  J Am Chem Soc       Date:  2014-06-24       Impact factor: 15.419

9.  2,5-Dibromo-indan-1-ol.

Authors:  Ismail Celik; Mehmet Akkurt; Makbule Yilmaz; Ahmet Tutar; Ramazan Erenler; Santiago García-Granda
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-08-25

10.  Enantioselective intramolecular C-H insertion reactions of donor-donor metal carbenoids.

Authors:  Cristian Soldi; Kellan N Lamb; Richard A Squitieri; Marcos González-López; Michael J Di Maso; Jared T Shaw
Journal:  J Am Chem Soc       Date:  2014-10-21       Impact factor: 15.419
  10 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.