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Literature DB >> 21548595

Total synthesis of epicoccin G.

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

Abstract

An expedient enantioselective total synthesis of epicoccin G and related dithiodiketopiperazines through a strategy featuring direct two-directional sulfenylation, photooxygenation, and Kornblum-DeLaMare rearrangement is described.

Entities: CellLine Chemical Disease Gene Species

Mesh：

Substances：
Piperazines
epicoccin G

Year: 2011 PMID： 21548595 PMCID： PMC3102137 DOI： 10.1021/ja2032635

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

17 in total

1. Piperafizines A and B, potentiators of cytotoxicity of vincristine.

Authors: H Kamei; M Oka; Y Hamagishi; K Tomita; M Konishi; T Oki
Journal: J Antibiot (Tokyo) Date: 1990-08 Impact factor: 2.649

Review 2. 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

3. 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

4. A total synthesis of sporidesmin A.

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

5. [Studies in the synthesis of the antibiotics gliotoxin, sporidesmin, aranotin, and chaetocin. IV. Preparation of epidithio-L-prolyl-L-proline anhydride].

Authors: E Ohler; H Poisel; F Tataruch; U Schmidt
Journal: Chem Ber Date: 1972

6. A total synthesis of gliotoxin.

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

7. First synthesis of the antifungal oidiolactone C from trans-communic acid: cytotoxic and antimicrobial activity in podolactone-related compounds.

Authors: Alejandro F Barrero; Siméon Arseniyadis; José F Quílez del Moral; M Mar Herrador; M Valdivia; D Jiménez
Journal: J Org Chem Date: 2002-04-19 Impact factor: 4.354

8. Enantioselective synthesis of gamma-hydroxyenones by chiral base-catalyzed Kornblum DeLaMare rearrangement.

Authors: Steven T Staben; Xin Linghu; F Dean Toste
Journal: J Am Chem Soc Date: 2006-10-04 Impact factor: 15.419

9. Pestalazines and pestalamides, bioactive metabolites from the plant pathogenic fungus Pestalotiopsis theae.

Authors: Gang Ding; Lihua Jiang; Liangdong Guo; Xulin Chen; Hua Zhang; Yongsheng Che
Journal: J Nat Prod Date: 2008-10-15 Impact factor: 4.050

10. 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

21 in total

1. A practical sulfenylation of 2,5-diketopiperazines.

Authors: K C Nicolaou; Denis Giguère; Sotirios Totokotsopoulos; Ya-Ping Sun
Journal: Angew Chem Int Ed Engl Date: 2011-12-07 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. 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

9. General approach for preparing epidithiodioxopiperazines from trioxopiperazine precursors: enantioselective total syntheses of (+)- and (-)-gliocladine C, (+)-leptosin D, (+)-T988C, (+)-bionectin A, and (+)-gliocladin A.

Authors: John E DeLorbe; David Horne; Richard Jove; Steven M Mennen; Sangkil Nam; Fang-Li Zhang; Larry E Overman
Journal: J Am Chem Soc Date: 2013-03-01 Impact factor: 15.419

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

Authors: Nicolas Boyer; Mohammad Movassaghi
Journal: Chem Sci Date: 2012-03-30 Impact factor: 9.825