Literature DB >> 22617016

Diastereocontrolled construction of pactamycin's complex ureido triol functional array.

Justin T Malinowski1, Stefan J McCarver, Jeffrey S Johnson.   

Abstract

An advanced intermediate in a projected synthesis of pactamycin has been prepared. Early installation of the C1-dimethylurea functionality allows for its participation in a diastereoselective, chelation-controlled addition of organometal nucleophiles to the C5 prochiral ketone. Four of the molecule's six stereocenters are set with a ketone functional handle provided for subsequent manipulation.

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Year:  2012        PMID： 22617016      PMCID： PMC3366368          DOI： 10.1021/ol301140c

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


  11 in total

1.  Dissecting the ribosomal inhibition mechanisms of edeine and pactamycin: the universally conserved residues G693 and C795 regulate P-site RNA binding.

Authors:  George Dinos; Daniel N Wilson; Yoshika Teraoka; Witold Szaflarski; Paola Fucini; Dimitrios Kalpaxis; Knud H Nierhaus
Journal:  Mol Cell       Date:  2004-01-16       Impact factor: 17.970

2.  Applications of CeCl(3) as an environmental friendly promoter in organic chemistry.

Authors:  Giuseppe Bartoli; Enrico Marcantoni; Mauro Marcolini; Letizia Sambri
Journal:  Chem Rev       Date:  2010-10-13       Impact factor: 60.622

3.  The structural basis for the action of the antibiotics tetracycline, pactamycin, and hygromycin B on the 30S ribosomal subunit.

Authors:  D E Brodersen; W M Clemons; A P Carter; R J Morgan-Warren; B T Wimberly; V Ramakrishnan
Journal:  Cell       Date:  2000-12-22       Impact factor: 41.582

4.  Concise total syntheses of palominol, dolabellatrienone, beta-araneosene, and isoedunol via an enantioselective Diels-Alder macrobicyclization.

Authors:  Scott A Snyder; E J Corey
Journal:  J Am Chem Soc       Date:  2006-01-25       Impact factor: 15.419

5.  Total synthesis of pactamycin.

Authors:  Stephen Hanessian; Ramkrishna Reddy Vakiti; Stéphane Dorich; Shyamapada Banerjee; Fabien Lecomte; Juan R DelValle; Jianbin Zhang; Benoît Deschênes-Simard
Journal:  Angew Chem Int Ed Engl       Date:  2011-03-02       Impact factor: 15.336

6.  The structure of pactamycin.

Authors:  P F Wiley; H K Jahnke; F MacKellar; R B Kelly; A D Argoudelis
Journal:  J Org Chem       Date:  1970-05       Impact factor: 4.354

7.  Total syntheses of epothilones B and D.

Authors:  J Mulzer; A Mantoulidis; E Ohler
Journal:  J Org Chem       Date:  2000-11-03       Impact factor: 4.354

8.  N-H insertion reactions of primary ureas: the synthesis of highly substituted imidazolones and imidazoles from diazocarbonyls.

Authors:  Sang-Hyeup Lee; Kazuhiro Yoshida; Hana Matsushita; Bruce Clapham; Guido Koch; Jürg Zimmermann; Kim D Janda
Journal:  J Org Chem       Date:  2004-12-10       Impact factor: 4.354

9.  Intramolecular carbolithiation reactions for the preparation of 3-alkenylpyrrolidines.

Authors:  Iain Coldham; Kathy N Price; Richard E Rathmell
Journal:  Org Biomol Chem       Date:  2003-06-21       Impact factor: 3.876

10.  Carbon-13 nuclear magnetic resonance assignments of pactamycin and related compounds.

Authors:  D D Weller; A Haber; K L Rinehart; P F Wiley
Journal:  J Antibiot (Tokyo)       Date:  1978-10       Impact factor: 2.649
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  9 in total

1.  Asymmetric Total Synthesis of the Indole Diterpene Alkaloid Paspaline.

Authors:  Robert J Sharpe; Jeffrey S Johnson
Journal:  J Org Chem       Date:  2015-10-02       Impact factor: 4.354

2.  Local Desymmetrization through Diastereotopic Group Selection: An Enabling Strategy for Natural Product Synthesis.

Authors:  Matthew A Horwitz; Jeffrey S Johnson
Journal:  European J Org Chem       Date:  2017-02-07

3.  Preparation and biological evaluation of synthetic and polymer-encapsulated congeners of the antitumor agent pactamycin: insight into functional group effects and biological activity.

Authors:  Robert J Sharpe; Justin T Malinowski; Federico Sorana; J Christopher Luft; Charles J Bowerman; Joseph M DeSimone; Jeffrey S Johnson
Journal:  Bioorg Med Chem       Date:  2015-02-21       Impact factor: 3.641

4.  Enantioselective synthesis of pactamycin, a complex antitumor antibiotic.

Authors:  Justin T Malinowski; Robert J Sharpe; Jeffrey S Johnson
Journal:  Science       Date:  2013-04-12       Impact factor: 47.728

5.  Mutasynthesis of fluorinated pactamycin analogues and their antimalarial activity.

Authors:  Khaled H Almabruk; Wanli Lu; Yuexin Li; Mostafa Abugreen; Jane X Kelly; Taifo Mahmud
Journal:  Org Lett       Date:  2013-03-22       Impact factor: 6.005

6.  Diastereoselective Synthesis of the Aminocyclitol Core of Jogyamycin via an Allene Aziridination Strategy.

Authors:  Nels C Gerstner; Christopher S Adams; R David Grigg; Maik Tretbar; Jared W Rigoli; Jennifer M Schomaker
Journal:  Org Lett       Date:  2016-01-07       Impact factor: 6.005

Review 7.  Strategies for the Syntheses of Pactamycin and Jogyamycin.

Authors:  Nels C Gerstner; Kate A Nicastri; Jennifer M Schomaker
Journal:  Angew Chem Int Ed Engl       Date:  2021-01-18       Impact factor: 15.336

8.  Oxidative allene amination for the synthesis of nitrogen-containing heterocycles.

Authors:  Josephine Eshon; Nels C Gerstner; Jennifer M Schomaker
Journal:  ARKIVOC       Date:  2018-11-26       Impact factor: 1.140

9.  Asymmetric synthesis of the aminocyclitol pactamycin, a universal translocation inhibitor.

Authors:  Robert J Sharpe; Justin T Malinowski; Jeffrey S Johnson
Journal:  J Am Chem Soc       Date:  2013-11-18       Impact factor: 15.419
  9 in total

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