Literature DB >> 20160945

Observations in the Synthesis of the Core of the Antitumor Illudins via an Enyne Ring Closing Metathesis Cascade.

Mohammad Movassaghi1, Grazia Piizzi, Dustin S Siegel, Giovanni Piersanti.   

Abstract

Observations concerning the synthesis of the core spirocyclic AB-ring system of illudins using an enyne ring closing metathesis (EYRCM) cascade are discussed. Substituent effects, in addition to optimization of the reaction conditions and the olefin tether for the key EYRCM reaction, are examined.

Entities:  

Year:  2009        PMID： 20160945      PMCID： PMC2766079          DOI： 10.1016/j.tetlet.2009.07.102

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


  22 in total

1.  FUNGAL METABOLITES. THE STRUCTURES OF THE NOVEL SESQUITERPENOIDS ILLUDIN-S AND -M.

Authors:  T C MCMORRIS; M ANCHEL
Journal:  J Am Chem Soc       Date:  1965-04-05       Impact factor: 15.419

2.  Enantioselective total synthesis of (-)-acylfulvene and (-)-irofulven.

Authors:  Mohammad Movassaghi; Grazia Piizzi; Dustin S Siegel; Giovanni Piersanti
Journal:  Angew Chem Int Ed Engl       Date:  2006-09-04       Impact factor: 15.336

3.  Production of Illudin M and of a Fourth Crystalline Compound by Clitocybe Illudens.

Authors:  M Anchel; A Hervey; W J Robbins
Journal:  Proc Natl Acad Sci U S A       Date:  1952-11       Impact factor: 11.205

4.  Depurinating acylfulvene-DNA adducts: characterizing cellular chemical reactions of a selective antitumor agent.

Authors:  Jiachang Gong; V G Vaidyanathan; Xiang Yu; Thomas W Kensler; Lisa A Peterson; Shana J Sturla
Journal:  J Am Chem Soc       Date:  2007-01-27       Impact factor: 15.419

5.  Irofulven as first line therapy in recurrent or metastatic gastric cancer: a phase II multicenter study by the Cancer Therapeutics Research Group (CTRG).

Authors:  W Yeo; M Boyer; H C Chung; S Y K Ong; R Lim; Benny Zee; B Ma; K C Lam; F K F Mo; E K W Ng; R Ho; S Clarke; J K Roh; P Beale; S Y Rha; H C Jeung; R Soo; B C Goh; A T C Chan
Journal:  Cancer Chemother Pharmacol       Date:  2006-06-17       Impact factor: 3.333

6.  (Hydroxymethyl)acylfulvene: an illudin derivative with superior antitumor properties.

Authors:  T C McMorris; M J Kelner; W Wang; J Yu; L A Estes; R Taetle
Journal:  J Nat Prod       Date:  1996-09       Impact factor: 4.050

7.  Investigating the role of stereochemistry in the activity of anticancer acylfulvenes: synthesis, reductase-mediated bioactivation, and cellular toxicity.

Authors:  Jiachang Gong; James F Neels; Xiang Yu; Thomas W Kensler; Lisa A Peterson; Shana J Sturla
Journal:  J Med Chem       Date:  2006-04-20       Impact factor: 7.446

8.  Synthesis and biological activity of enantiomers of antitumor irofulven.

Authors:  Trevor C McMorris; Michael D Staake; Michael J Kelner
Journal:  J Org Chem       Date:  2004-02-06       Impact factor: 4.354

9.  Ovarian tumor growth regression using a combination of vascular targeting agents anginex or topomimetic 0118 and the chemotherapeutic irofulven.

Authors:  Ruud P M Dings; Emily S Van Laar; Jeremy Webber; Yan Zhang; Robert J Griffin; Stephen J Waters; John R MacDonald; Kevin H Mayo
Journal:  Cancer Lett       Date:  2008-04-01       Impact factor: 8.679

10.  Phase I and pharmacokinetic study of irofulven administered weekly or biweekly in advanced solid tumor patients.

Authors:  Jérôme Alexandre; Eric Raymond; Mahmoud Ould Kaci; Etienne C Brain; François Lokiec; Carmen Kahatt; Sandrine Faivre; Alejandro Yovine; François Goldwasser; Sheri L Smith; John R MacDonald; Jean-Louis Misset; Esteban Cvitkovic
Journal:  Clin Cancer Res       Date:  2004-05-15       Impact factor: 12.531
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  1 in total

1.  Enantioselective total synthesis of (-)-acylfulvene and (-)-irofulven.

Authors:  Dustin S Siegel; Grazia Piizzi; Giovanni Piersanti; Mohammad Movassaghi
Journal:  J Org Chem       Date:  2009-12-18       Impact factor: 4.354
  1 in total

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