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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.

Abstract

A substituted 2R-allyl-3S-methylproline ethyl ester suitable for elaboration to n class="Chemical">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: Chemical Disease Gene Species

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

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

1. The isolation of brevianamide A from Penicillium ochraceum.

2. New paraherquamide antibiotics with anthelmintic activity.

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

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

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

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

8. Anthelmintic activity of paraherquamide in sheep.

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

10. Anthelmintic activity of paraherquamide in calves.

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