Literature DB >> 20336192

Studies Towards Paraherquamides E & F and Related C-labeled Putative Biosynthetic Intermediates: Stereocontrolled Synthesis of the α-Alkyl-β-Methylproline Ring System.

Konrad Sommer1, Robert M Williams.   

Abstract

A substituted 2R-allyl-3S-methylproline ethyl ester suitable for elaboration to paraherquamides E, F and related (13)C-labelled putative biosynthesis intermediates have been prepared efficiently in six steps and 24% overall yield. The key steps are a 5-exo-trig cyclization of a zinc enolate on an unactivated alkene and a stereocontrolled alkylation of the enolate formed from 3S-methyl-pyrrolidine-1,2R-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester.

Entities:  

Year:  2008        PMID： 20336192      PMCID： PMC2844772          DOI： 10.1016/j.tet.2008.05.068

Source DB:  PubMed          Journal:  Tetrahedron        ISSN： 0040-4020            Impact factor:   2.457


  36 in total

1.  The isolation of brevianamide A from Penicillium ochraceum.

Authors:  J E Robbers; J W Straus
Journal:  Lloydia       Date:  1975 Jul-Aug

2.  New paraherquamide antibiotics with anthelmintic activity.

Authors:  S E Blanchflower; R M Banks; J R Everett; B R Manger; C Reading
Journal:  J Antibiot (Tokyo)       Date:  1991-05       Impact factor: 2.649

3.  A concise total synthesis of the notoamides C and D.

Authors:  Alan W Grubbs; Gerald D Artman; Sachiko Tsukamoto; Robert M Williams
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

4.  Disposition of Mycophenolic Acid, Brevianamide A, Asperphenamate, and Ergosterol in Solid Cultures of Penicillium brevicompactum.

Authors:  B A Bird; I M Campbell
Journal:  Appl Environ Microbiol       Date:  1982-02       Impact factor: 4.792

5.  Novel anthelmintic metabolites from an Aspergillus species; the aspergillimides.

Authors:  R M Banks; S E Blanchflower; J R Everett; B R Manger; C Reading
Journal:  J Antibiot (Tokyo)       Date:  1997-10       Impact factor: 2.649

6.  Asymmetric, Stereocontrolled Total Synthesis of Paraherquamide A This work was supported by the NIH (Grant CA 70375). The Japanese Society for the Promotion of Science (JSPS) is acknowledged for providing support to H.T. Mass spectra were obtained on instruments supported by the NIH Shared Instrumentation Grant (GM 49631). We also wish to thank Dr. Timothy Blizzard (Merck & Co.) for providing an authentic sample of natural paraherquamide A. We also wish to acknowledge Dr. Byung H. Lee (Pharmacia-Upjohn Co.) for providing NMR spectra and an authentic specimen of 14-oxoparaherquamide B. We also wish to thank Dr. Alfredo Vazquez for assistance with purification and characterization of synthetic paraherquamide A.

Authors: 
Journal:  Angew Chem Int Ed Engl       Date:  2000-07-17       Impact factor: 15.336

7.  Sclerotiamide: a new member of the paraherquamide class with potent antiinsectan activity from the sclerotia of Aspergillus sclerotiorum.

Authors:  A C Whyte; J B Gloer; D T Wicklow; P F Dowdw
Journal:  J Nat Prod       Date:  1996-11       Impact factor: 4.050

8.  Anthelmintic activity of paraherquamide in sheep.

Authors:  W L Shoop; J R Egerton; C H Eary; D Suhayda
Journal:  J Parasitol       Date:  1990-06       Impact factor: 1.276

9.  Concise, Biomimetic Total Synthesis of d,l-Marcfortine C.

Authors:  Thomas J Greshock; Alan W Grubbs; Robert M Williams
Journal:  Tetrahedron       Date:  2007-07-02       Impact factor: 2.457

10.  Anthelmintic activity of paraherquamide in calves.

Authors:  W L Shoop; B F Michael; H W Haines; C H Eary
Journal:  Vet Parasitol       Date:  1992-07       Impact factor: 2.738
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  1 in total

1.  Recent Progress on the Stereoselective Synthesis of Cyclic Quaternary alpha-Amino Acids.

Authors:  Carlos Cativiela; Mario Ordóñez
Journal:  Tetrahedron Asymmetry       Date:  2009-01-30
  1 in total

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