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Literature DB >> 20866039

General approach to epipolythiodiketopiperazine alkaloids: total synthesis of (+)-chaetocins A and C and (+)-12,12'-dideoxychetracin A.

Abstract

A highly stereoselective and systematic strategy for the introduction of polysulfides in the synthesis of epipolythiodiketopiperazines is described. We report the first total synthesis of dimeric epitri- and epitetrathiodiketopiperazines.

Entities: Chemical Disease Species

Mesh：

Substances：
Piperazines
chaetocin

Year: 2010 PMID： 20866039 PMCID： PMC2987664 DOI： 10.1021/ja106869s

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

15 in total

1. Concise total synthesis of (-)-calycanthine, (+)-chimonanthine, and (+)-folicanthine.

Authors: Mohammad Movassaghi; Michael A Schmidt
Journal: Angew Chem Int Ed Engl Date: 2007 Impact factor: 15.336

2. Concise total synthesis of (+)-WIN 64821 and (-)-ditryptophenaline.

Authors: Mohammad Movassaghi; Michael A Schmidt; James A Ashenhurst
Journal: Angew Chem Int Ed Engl Date: 2008 Impact factor: 15.336

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4. Total synthesis of (+)-chaetocin and its analogues: their histone methyltransferase G9a inhibitory activity.

Authors: Eriko Iwasa; Yoshitaka Hamashima; Shinya Fujishiro; Eisuke Higuchi; Akihiro Ito; Minoru Yoshida; Mikiko Sodeoka
Journal: J Am Chem Soc Date: 2010-03-31 Impact factor: 15.419

5. A short synthesis of aromatic analogues of the aranotins.

Authors: D L Coffen; D A Katonak; N R Nelson; F D Sancilio
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6. Approaches to analogues of dehydrogliotoxin. 6. An efficient synthesis of a gliotoxin analogue with anti-reverse transcriptase activity.

Authors: H C Ottenheijm; J D Herscheid; G P Kerkhoff; T F Spande
Journal: J Org Chem Date: 1976-10-15 Impact factor: 4.354

7. 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

8. 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

9. 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

10. Sirodesmins A, B, C, and B, antiviral epipolythiopiperazine-2,5-diones of fungal origin: X-ray analysis of sirodesmin A diacetate.

Authors: P J Curtis; D Greatbanks; B Hesp; A F Cameron; A A Freer
Journal: J Chem Soc Perkin 1 Date: 1977

39 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

2. Concise Total Synthesis of (+)-Asperazine, (+)-Pestalazine A, and (+)-iso-Pestalazine A. Structure Revision of (+)-Pestalazine A.

Authors: Richard P Loach; Owen S Fenton; Mohammad Movassaghi
Journal: J Am Chem Soc Date: 2016-01-19 Impact factor: 15.419

3. Total synthesis of (+)-gliocladin C enabled by visible-light photoredox catalysis.

Authors: Laura Furst; Jagan M R Narayanam; Corey R J Stephenson
Journal: Angew Chem Int Ed Engl Date: 2011-07-12 Impact factor: 15.336

4. Application of diazene-directed fragment assembly to the total synthesis and stereochemical assignment of (+)-desmethyl-meso-chimonanthine and related heterodimeric alkaloids.

Authors: Stephen P Lathrop; Mohammad Movassaghi
Journal: Chem Sci Date: 2014-01-01 Impact factor: 9.825

5. Bürgenstock 2011: a stereochemical sojourn.

Authors: Mark S Taylor
Journal: Nat Chem Date: 2011-08-23 Impact factor: 24.427

6. Cytotoxic epipolythiodioxopiperazine alkaloids from filamentous fungi of the Bionectriaceae.

Authors: Mario Figueroa; Tyler N Graf; Sloan Ayers; Audrey F Adcock; David J Kroll; Jilai Yang; Steven M Swanson; Ulyana Munoz-Acuna; Esperanza J Carcache de Blanco; Rajesh Agrawal; Mansukh C Wani; Blaise A Darveaux; Cedric J Pearce; Nicholas H Oberlies
Journal: J Antibiot (Tokyo) Date: 2012-09-12 Impact factor: 2.649

7. 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

Review 8. Epidithiodioxopiperazines. occurrence, synthesis and biogenesis.

Authors: Timothy R Welch; Robert M Williams
Journal: Nat Prod Rep Date: 2014-10 Impact factor: 13.423

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