Literature DB >> 22053119

First total synthesis of (+)-Vedelianin, a potent antiproliferative agent.

Joseph J Topczewski1, David F Wiemer.   

Abstract

The total synthesis of (+)-vedelianin has been accomplished in 18 steps from vanillin. Preparation of a key intermediate in nonracemic form through a Shi epoxidation has allowed determination of the absolute stereochemistry of the natural product as the (2S, 3R, 4aR, 9aR)-isomer.

Entities:  

Year:  2011        PMID： 22053119      PMCID： PMC3204860          DOI： 10.1016/j.tetlet.2011.01.137

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


  14 in total

1.  Synthesis and structure-activity studies of schweinfurthin B analogs: Evidence for the importance of a D-ring hydrogen bond donor in expression of differential cytotoxicity.

Authors:  Jeffrey D Neighbors; Maya S Salnikova; John A Beutler; David F Wiemer
Journal:  Bioorg Med Chem       Date:  2005-11-14       Impact factor: 3.641

2.  Synthesis of nonracemic 3-deoxyschweinfurthin B.

Authors:  Jeffrey D Neighbors; John A Beutler; David F Wiemer
Journal:  J Org Chem       Date:  2005-02-04       Impact factor: 4.354

3.  Synthetic applications of the carbonyl generating Grob fragmentation.

Authors:  Kathrin Prantz; Johann Mulzer
Journal:  Chem Rev       Date:  2010-06-09       Impact factor: 60.622

4.  Pentacyclic triterpenes. Part 5: synthesis and SAR study of corosolic acid derivatives as inhibitors of glycogen phosphorylases.

Authors:  Xiaoan Wen; Jun Xia; Keguang Cheng; Liying Zhang; Pu Zhang; Jun Liu; Luyong Zhang; Peizhou Ni; Hongbin Sun
Journal:  Bioorg Med Chem Lett       Date:  2007-08-28       Impact factor: 2.823

5.  Cytotoxic geranyl stilbenes from Macaranga schweinfurthii.

Authors:  J A Beutler; R H Shoemaker; T Johnson; M R Boyd
Journal:  J Nat Prod       Date:  1998-12       Impact factor: 4.050

6.  Antiproliferative prenylated stilbenes and flavonoids from Macaranga alnifolia from the Madagascar rainforest.

Authors:  Brent J Yoder; Shugeng Cao; Andrew Norris; James S Miller; Fidy Ratovoson; Jeremi Razafitsalama; Rabodo Andriantsiferana; Vincent E Rasamison; David G I Kingston
Journal:  J Nat Prod       Date:  2007-02-28       Impact factor: 4.050

7.  Total synthesis of (R,R,R)- and (S,S,S)-schweinfurthin F: differences of bioactivity in the enantiomeric series.

Authors:  Nolan R Mente; Andrew J Wiemer; Jeffrey D Neighbors; John A Beutler; Raymond J Hohl; David F Wiemer
Journal:  Bioorg Med Chem Lett       Date:  2006-12-12       Impact factor: 2.823

8.  Organocatalytic asymmetric epoxidation of olefins by chiral ketones.

Authors:  Yian Shi
Journal:  Acc Chem Res       Date:  2004-08       Impact factor: 22.384

9.  Total synthesis of (+)-schweinfurthins B and E.

Authors:  Joseph J Topczewski; Jeffrey D Neighbors; David F Wiemer
Journal:  J Org Chem       Date:  2009-09-18       Impact factor: 4.354

10.  BF3 x Et2O-mediated cascade cyclizations: synthesis of schweinfurthins F and G.

Authors:  Nolan R Mente; Jeffrey D Neighbors; David F Wiemer
Journal:  J Org Chem       Date:  2008-09-17       Impact factor: 4.354
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  8 in total

1.  Synthesis and structure activity relationships of schweinfurthin indoles.

Authors:  John G Kodet; John A Beutler; David F Wiemer
Journal:  Bioorg Med Chem       Date:  2014-03-06       Impact factor: 3.641

2.  Relevance of the C-5 position to schweinfurthin induced cytotoxicity.

Authors:  Joseph J Topczewski; Michael P Callahan; John G Kodet; Jery D Inbarasu; Nolan R Mente; John A Beutler; David F Wiemer
Journal:  Bioorg Med Chem       Date:  2011-10-19       Impact factor: 3.641

3.  Substitution of a triazole for the central olefin in biologically active stilbenes.

Authors:  David P Stockdale; John A Beutler; David F Wiemer
Journal:  Bioorg Med Chem Lett       Date:  2022-09-09       Impact factor: 2.940

4.  Synthesis of amide isosteres of schweinfurthin-based stilbenes.

Authors:  David P Stockdale; John A Beutler; David F Wiemer
Journal:  Bioorg Med Chem       Date:  2017-08-09       Impact factor: 3.641

5.  Stilbenes as κ-selective, non-nitrogenous opioid receptor antagonists.

Authors:  Alyssa M Hartung; John A Beutler; Hernán A Navarro; David F Wiemer; Jeffrey D Neighbors
Journal:  J Nat Prod       Date:  2014-01-23       Impact factor: 4.050

6.  UHPLC-HESI-OT-MS-MS Biomolecules Profiling, Antioxidant and Antibacterial Activity of the "Orange-Yellow Resin" from Zuccagnia punctata Cav.

Authors:  Jessica Gómez; Mario J Simirgiotis; Sofía Manrique; Beatriz Lima; Jorge Bórquez; Gabriela E Feresin; Alejandro Tapia
Journal:  Antioxidants (Basel)       Date:  2020-02-01

7.  Synthesis of a Coumarin-Based Analogue of Schweinfurthin F.

Authors:  Chloe M Schroeder; Patrick N Dey; John A Beutler; David F Wiemer
Journal:  J Org Chem       Date:  2021-10-29       Impact factor: 4.354

Review 8.  Schweinfurthins A-Q: isolation, synthesis, and biochemical properties.

Authors:  Dipesh S Harmalkar; Jyotirling R Mali; Aneesh Sivaraman; Yongseok Choi; Kyeong Lee
Journal:  RSC Adv       Date:  2018-06-08       Impact factor: 4.036
  8 in total

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