Literature DB >> 19572306

A symmetry-based concise formal synthesis of platencin, a novel lead against "superbugs".

Arun K Ghosh1, Kai Xi.   

Abstract

Quick access: A concise and efficient formal synthesis of platencin has been accomplished in nine steps from a commercially available starting material. The synthesis utilized only one protecting group. The base-catalyzed Michael cyclization of precursor 1 afforded the key diketone 2, which was converted into the desired core structure 4 via the radical intermediate 3.

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Year:  2009        PMID： 19572306      PMCID： PMC3518310          DOI： 10.1002/anie.200902338

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  22 in total

Review 1.  Empirical antibacterial drug discovery--foundation in natural products.

Authors:  Sheo B Singh; John F Barrett
Journal:  Biochem Pharmacol       Date:  2006-01-19       Impact factor: 5.858

Review 2.  Platensimycin, a new antibiotic and "superbug challenger" from nature.

Authors:  Dieter Häbich; Franz von Nussbaum
Journal:  ChemMedChem       Date:  2006-09       Impact factor: 3.466

3.  Enantioselective route to platensimycin: an intramolecular Robinson annulation approach.

Authors:  Pingfan Li; Joshua N Payette; Hisashi Yamamoto
Journal:  J Am Chem Soc       Date:  2007-07-14       Impact factor: 15.419

Review 4.  Natural products--the future scaffolds for novel antibiotics?

Authors:  Mark S Butler; Antony D Buss
Journal:  Biochem Pharmacol       Date:  2005-11-14       Impact factor: 5.858

5.  Aldol condensation versus conjugate addition: intramolecular cyclization using a combination of Lewis acid and 1,2-diol.

Authors:  S Yamada; H Suemune
Journal:  Chem Pharm Bull (Tokyo)       Date:  2000-08       Impact factor: 1.645

6.  Formal synthesis of (+/-)-platensimycin.

Authors:  Yefen Zou; Chun-Hsing Chen; Christopher D Taylor; Bruce M Foxman; Barry B Snider
Journal:  Org Lett       Date:  2007-04-04       Impact factor: 6.005

7.  Isolation, structure, and absolute stereochemistry of platensimycin, a broad spectrum antibiotic discovered using an antisense differential sensitivity strategy.

Authors:  Sheo B Singh; Hiranthi Jayasuriya; John G Ondeyka; Kithsiri B Herath; Chaowei Zhang; Deborah L Zink; Nancy N Tsou; Richard G Ball; Angela Basilio; Olga Genilloud; Maria Teresa Diez; Francisca Vicente; Fernando Pelaez; Katherine Young; Jun Wang
Journal:  J Am Chem Soc       Date:  2006-09-13       Impact factor: 15.419

8.  Platensimycin is a selective FabF inhibitor with potent antibiotic properties.

Authors:  Jun Wang; Stephen M Soisson; Katherine Young; Wesley Shoop; Srinivas Kodali; Andrew Galgoci; Ronald Painter; Gopalakrishnan Parthasarathy; Yui S Tang; Richard Cummings; Sookhee Ha; Karen Dorso; Mary Motyl; Hiranthi Jayasuriya; John Ondeyka; Kithsiri Herath; Chaowei Zhang; Lorraine Hernandez; John Allocco; Angela Basilio; José R Tormo; Olga Genilloud; Francisca Vicente; Fernando Pelaez; Lawrence Colwell; Sang Ho Lee; Bruce Michael; Thomas Felcetto; Charles Gill; Lynn L Silver; Jeffery D Hermes; Ken Bartizal; John Barrett; Dennis Schmatz; Joseph W Becker; Doris Cully; Sheo B Singh
Journal:  Nature       Date:  2006-05-18       Impact factor: 49.962

9.  Formal total synthesis of platencin.

Authors:  Georgy N Varseev; Martin E Maier
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

10.  Discovery of platencin, a dual FabF and FabH inhibitor with in vivo antibiotic properties.

Authors:  Jun Wang; Srinivas Kodali; Sang Ho Lee; Andrew Galgoci; Ronald Painter; Karen Dorso; Fred Racine; Mary Motyl; Lorraine Hernandez; Elizabeth Tinney; Steven L Colletti; Kithsiri Herath; Richard Cummings; Oscar Salazar; Ignacio González; Angela Basilio; Francisca Vicente; Olga Genilloud; Fernando Pelaez; Hiranthi Jayasuriya; Katherine Young; Doris F Cully; Sheo B Singh
Journal:  Proc Natl Acad Sci U S A       Date:  2007-04-24       Impact factor: 11.205
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  6 in total

Review 1.  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

Review 2.  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

3.  Capturing the essence of organic synthesis: from bioactive natural products to designed molecules in today's medicine.

Authors:  Arun K Ghosh
Journal:  J Org Chem       Date:  2010-10-11       Impact factor: 4.354

4.  Short Enantioselective Formal Synthesis of (-)-Platencin.

Authors:  Christian Defieber; Justin T Mohr; Gennadii A Grabovyi; Brian M Stoltz
Journal:  Synthesis (Stuttg)       Date:  2018-07-23       Impact factor: 3.157

5.  Synthesis and antibacterial properties of (-)-nor-platencin.

Authors:  Olga V Barykina; Kerri L Rossi; Michael J Rybak; Barry B Snider
Journal:  Org Lett       Date:  2009-11-19       Impact factor: 6.005

Review 6.  Antibiotics and bacterial resistance in the 21st century.

Authors:  Richard J Fair; Yitzhak Tor
Journal:  Perspect Medicin Chem       Date:  2014-08-28
  6 in total

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