Literature DB >> 18001051

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

Larry E Overman1, Takaaki Sato.   

Abstract

Functionalization of the angular methine carbon of hydroxyproline-derived dioxopiperazines by a radical-promoted C-H bond oxidation, which is directed by a proximal (bromomethyl)silyl group, is described. This regioselective oxidation is the key step in a new synthesis of epidithiodioxopiperazines.

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Year:  2007        PMID： 18001051     DOI： 10.1021/ol702518t

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  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

2.  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

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

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

Authors:  Henry R Kilgore; Chase R Olsson; Kyan A D'Angelo; Mohammad Movassaghi; Ronald T Raines
Journal:  J Am Chem Soc       Date:  2020-08-21       Impact factor: 15.419

5.  A Modular Construction of Epidithiodiketopiperazines.

Authors:  Thomas N Snaddon; Toya D Scaggs; Colin M Pearson; James W B Fyfe
Journal:  Org Lett       Date:  2019-06-11       Impact factor: 6.005

Review 6.  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

7.  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

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

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

9.  Stereospecific total synthesis of somocystinamide A.

Authors:  Takashi L Suyama; William H Gerwick
Journal:  Org Lett       Date:  2008-09-13       Impact factor: 6.005

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
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