Literature DB >> 20210309

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

Eriko Iwasa1, Yoshitaka Hamashima, Shinya Fujishiro, Eisuke Higuchi, Akihiro Ito, Minoru Yoshida, Mikiko Sodeoka.   

Abstract

The first total synthesis of (+)-chaetocin has been accomplished in nine steps starting from known N-Cbz-N-Me-serine using radical alpha-bromination reaction of diketopiperazine 10 and Co(I)-mediated reductive dimerization reaction of 12 as key reactions. The enantiomers show comparable inhibitory activity toward histone methyltransferase (HMT) G9a, but analogues without the sulfur functionality are inactive.

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Year:  2010        PMID： 20210309     DOI： 10.1021/ja101280p

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


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

Authors:  Justin Kim; Mohammad Movassaghi
Journal:  J Am Chem Soc       Date:  2010-10-20       Impact factor: 15.419

4.  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

5.  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

Review 6.  The promise and failures of epigenetic therapies for cancer treatment.

Authors:  Pasano Bojang; Kenneth S Ramos
Journal:  Cancer Treat Rev       Date:  2013-07-05       Impact factor: 12.111

7.  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

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
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