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Literature DB >> 22162254

A practical sulfenylation of 2,5-diketopiperazines.

K C Nicolaou¹, Denis Giguère, Sotirios Totokotsopoulos, Ya-Ping Sun.

Abstract

Entities: Chemical Disease Gene

Mesh：

Substances：

Year: 2011 PMID： 22162254 PMCID： PMC3348727 DOI： 10.1002/anie.201107623

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

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18 in total

Review 1. The epipolythiodioxopiperazine (ETP) class of fungal toxins: distribution, mode of action, functions and biosynthesis.

Authors: Donald M Gardiner; Paul Waring; Barbara J Howlett
Journal: Microbiology Date: 2005-04 Impact factor: 2.777

2. A total synthesis of dehydrogliotoxin.

Authors: Y Kishi; T Fukuyama; S Nakatsuka
Journal: J Am Chem Soc Date: 1973-09-19 Impact factor: 15.419

3. A total synthesis of gliotoxin.

Authors: T Fukuyama; Y Kishi
Journal: J Am Chem Soc Date: 1976-10-13 Impact factor: 15.419

4. Identification of a specific inhibitor of the histone methyltransferase SU(VAR)3-9.

Authors: Dorothea Greiner; Tiziana Bonaldi; Ragnhild Eskeland; Ernst Roemer; Axel Imhof
Journal: Nat Chem Biol Date: 2005-07-17 Impact factor: 15.040

5. A unified strategy targeting the thiodiketopiperazine mycotoxins exserohilone, gliotoxin, the epicoccins, the epicorazines, rostratin A and aranotin.

Authors: Ulrike Gross; Martin Nieger; Stefan Bräse
Journal: Chemistry Date: 2010-08-31 Impact factor: 5.236

6. Chaetocin: a promising new antimyeloma agent with in vitro and in vivo activity mediated via imposition of oxidative stress.

Authors: Crescent R Isham; Jennifer D Tibodeau; Wendy Jin; Ruifang Xu; Michael M Timm; Keith C Bible
Journal: Blood Date: 2006-11-07 Impact factor: 22.113

7. Total synthesis of (+)-11,11'-dideoxyverticillin A.

Authors: Justin Kim; James A Ashenhurst; Mohammad Movassaghi
Journal: Science Date: 2009-04-10 Impact factor: 47.728

8. [Amino acids and peptides. VII. Studies on the synthesis of 3,6-epidithio-2,5-dioxopiperazine antibiotics: gliotoxin, sporidesmin, aranotin, chaetocin, and verticillin. VII. The introduction of oxygen into prolyl-prolinanhydride via lead acetate: a new approach to the epidisulfide of prolyl-prolinanhydride].

Authors: E Ohler; F Tataruch; U Schmidt
Journal: Chem Ber Date: 1973

9. Antiviral activity of N, N'-dimethyl-epidithiapiperazinedione, a synthetic compound related to the gliotoxins, LL-S88alpha and beta, chetomin and the sporidesmins.

Authors: P W Trown
Journal: Biochem Biophys Res Commun Date: 1968-11-08 Impact factor: 3.575

10. Construction of epidithiodioxopiperazines by directed oxidation of hydroxyproline-derived dioxopiperazines.

Authors: Larry E Overman; Takaaki Sato
Journal: Org Lett Date: 2007-11-15 Impact factor: 6.005

15 in total

Review 1. 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

2. Synthesis and biological evaluation of epidithio-, epitetrathio-, and bis-(methylthio)diketopiperazines: synthetic methodology, enantioselective total synthesis of epicoccin G, 8,8'-epi-ent-rostratin B, gliotoxin, gliotoxin G, emethallicin E, and haematocin and discovery of new antiviral and antimalarial agents.

Authors: K C Nicolaou; Min Lu; Sotirios Totokotsopoulos; Philipp Heretsch; Denis Giguère; Ya-Ping Sun; David Sarlah; Thu H Nguyen; Ian C Wolf; Donald F Smee; Craig W Day; Selina Bopp; Elizabeth A Winzeler
Journal: J Am Chem Soc Date: 2012-10-04 Impact factor: 15.419

A practical sulfenylation of 2,5-diketopiperazines.

Review 1. The epipolythiodioxopiperazine (ETP) class of fungal toxins: distribution, mode of action, functions and biosynthesis.

2. A total synthesis of dehydrogliotoxin.

3. A total synthesis of gliotoxin.

4. Identification of a specific inhibitor of the histone methyltransferase SU(VAR)3-9.

5. A unified strategy targeting the thiodiketopiperazine mycotoxins exserohilone, gliotoxin, the epicoccins, the epicorazines, rostratin A and aranotin.

6. Chaetocin: a promising new antimyeloma agent with in vitro and in vivo activity mediated via imposition of oxidative stress.

7. Total synthesis of (+)-11,11'-dideoxyverticillin A.

9. Antiviral activity of N, N'-dimethyl-epidithiapiperazinedione, a synthetic compound related to the gliotoxins, LL-S88alpha and beta, chetomin and the sporidesmins.

10. Construction of epidithiodioxopiperazines by directed oxidation of hydroxyproline-derived dioxopiperazines.

Review 1. Constructing molecular complexity and diversity: total synthesis of natural products of biological and medicinal importance.

3. n→π* Interactions Modulate the Disulfide Reduction Potential of Epidithiodiketopiperazines.

4. A Modular Construction of Epidithiodiketopiperazines.

Review 5. A brief history of antibiotics and select advances in their synthesis.

6. Enantioselective total synthesis of plectosphaeroic acid B.

7. Concise Total Synthesis of (+)-Gliocladins B and C.

8. Concise Total Synthesis of (+)-Luteoalbusins A and B.

9. Concise Total Synthesis of (+)-Bionectins A and C.

10. Synthesis and Anticancer Activity of Epipolythiodiketopiperazine Alkaloids.