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Literature DB >> 23208736

How thiostrepton was made in the laboratory.

Abstract

Thiostrepton, a powerful antibiotic belonging to the thiopeptide class, was synthesized in the laboratory for the first time in 2004 through an arduous campaign involving novel strategies and tactics, scenic detours, and unexpected roadblocks. In this Review the author narrates the long journey to success, not so dissimilar to Odysseus' return voyage to Ithaca, full of adventure, knowledge, and wisdom.

Entities: Chemical Disease Gene Species

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Substances：

Year: 2012 PMID： 23208736 PMCID： PMC3515631 DOI： 10.1002/anie.201205576

Source DB: PubMed Journal: Angew Chem Int Ed Engl ISSN： 1433-7851 Impact factor: 15.336

36 in total

1. A Mild and Effective Method for the Transesterification of Carboxylic Acid Esters P.B. and R.M. are grateful to the Land Baden-Württemberg for a scholarship from the Landesgraduiertenförderung.

Authors: Patrick Baumhof; Ralph Mazitschek; Athanassios Giannis
Journal: Angew Chem Int Ed Engl Date: 2001-10-01 Impact factor: 15.336

Review 2. Constructing molecular complexity and diversity: total synthesis of natural products of biological and medicinal importance.

Authors: K C Nicolaou; Christopher R H Hale; Christian Nilewski; Heraklidia A Ioannidou
Journal: Chem Soc Rev Date: 2012-06-28 Impact factor: 54.564

3. A mild and selective method for the hydrolysis of esters with trimethyltin hydroxide.

Authors: K C Nicolaou; Anthony A Estrada; Mark Zak; Sang Hyup Lee; Brian S Safina
Journal: Angew Chem Int Ed Engl Date: 2005-02-18 Impact factor: 15.336

4. Total synthesis of the thiazolyl peptide GE2270 A.

Authors: H Martin Müller; Oscar Delgado; Thorsten Bach
Journal: Angew Chem Int Ed Engl Date: 2007 Impact factor: 15.336

Review 5. From amino acids to heteroaromatics--thiopeptide antibiotics, nature's heterocyclic peptides.

Authors: Rachael A Hughes; Christopher J Moody
Journal: Angew Chem Int Ed Engl Date: 2007 Impact factor: 15.336

6. Effect of lasalocid, monensin and thiopeptin on rumen protozoa.

Authors: S M Dennis; T G Nagaraja; A D Dayton
Journal: Res Vet Sci Date: 1986-09 Impact factor: 2.534

7. 13C NMR study of thiostrepton and thiopeptin components.

Authors: O D Hensens; G Albers-Schönberg
Journal: J Antibiot (Tokyo) Date: 1983-07 Impact factor: 2.649

8. Suppressive effect of antibiotic siomycin on antibody production.

Authors: Motoi Ueno; Satoko Furukawa; Fumie Abe; Michiko Ushioda; Kiyotaka Fujine; Shigeru Johki; Hidetaka Hatori; Hirotsugu Ueda
Journal: J Antibiot (Tokyo) Date: 2004-09 Impact factor: 2.649

9. Total synthesis of thiostrepton. Retrosynthetic analysis and construction of key building blocks.

Authors: K C Nicolaou; Brian S Safina; Mark Zak; Sang Hyup Lee; Marta Nevalainen; Marco Bella; Anthony A Estrada; Christian Funke; Frédéric J Zécri; Stephan Bulat
Journal: J Am Chem Soc Date: 2005-08-10 Impact factor: 15.419

6 in total

Review 1. A brief history of antibiotics and select advances in their synthesis.

Authors: Kyriacos C Nicolaou; Stephan Rigol
Journal: J Antibiot (Tokyo) Date: 2017-07-05 Impact factor: 2.649

2. Cobalt(III)-Catalyzed C-H Amidation of Dehydroalanine for the Site-Selective Structural Diversification of Thiostrepton.

Authors: Ryan J Scamp; Edward deRamon; Eric K Paulson; Scott J Miller; Jonathan A Ellman
Journal: Angew Chem Int Ed Engl Date: 2019-11-27 Impact factor: 15.336

3. Site- and Stereoselective Chemical Editing of Thiostrepton by Rh-Catalyzed Conjugate Arylation: New Analogues and Collateral Enantioselective Synthesis of Amino Acids.

Authors: Hanna M Key; Scott J Miller
Journal: J Am Chem Soc Date: 2017-10-20 Impact factor: 15.419