Literature DB >> 17407302

Formal synthesis of (+/-)-platensimycin.

Yefen Zou1, Chun-Hsing Chen, Christopher D Taylor, Bruce M Foxman, Barry B Snider.   

Abstract

[reaction: see text] Reductive alkylation of 5-methoxy-1-tetralone (6) with 2,3-dibromopropene gave an equilibrium mixture of bicyclic diones 7 (51%) and 8 (35%). Radical cyclization of 7 afforded tricyclic dione 5 (84%), which was reduced, cyclized, and dehydrated to give tetracyclic alkene 13 in 63% yield. Allylic oxidation of 13 with SeO2 and activated MnO2 afforded enone 2 in 85% yield, thereby completing a short formal synthesis of (+/-)-platensimycin.

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Year:  2007        PMID： 17407302      PMCID： PMC2518405          DOI： 10.1021/ol070563g

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


  4 in total

Review 1.  Platensimycin, a new antibiotic and "superbug challenger" from nature.

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

2.  Total synthesis of platensimycin.

Authors:  K C Nicolaou; Ang Li; David J Edmonds
Journal:  Angew Chem Int Ed Engl       Date:  2006-10-27       Impact factor: 15.336

3.  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

4.  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
  4 in total
  14 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

2.  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 3.  Recent advances in the chemistry and biology of naturally occurring antibiotics.

Authors:  K C Nicolaou; Jason S Chen; David J Edmonds; Anthony A Estrada
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

Review 4.  Navigating the Chiral Pool in the Total Synthesis of Complex Terpene Natural Products.

Authors:  Zachary G Brill; Matthew L Condakes; Chi P Ting; Thomas J Maimone
Journal:  Chem Rev       Date:  2017-03-15       Impact factor: 60.622

Review 5.  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

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

Authors:  Arun K Ghosh; Kai Xi
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

7.  Total synthesis of platensimycin and related natural products.

Authors:  K C Nicolaou; Ang Li; David J Edmonds; G Scott Tria; Shelby P Ellery
Journal:  J Am Chem Soc       Date:  2009-11-25       Impact factor: 15.419

8.  Total syntheses of (+/-)-platencin and (-)-platencin.

Authors:  K C Nicolaou; G Scott Tria; David J Edmonds; Moumita Kar
Journal:  J Am Chem Soc       Date:  2009-11-04       Impact factor: 15.419

9.  Total synthesis of (-)-platensimycin, a novel antibacterial agent.

Authors:  Arun K Ghosh; Kai Xi
Journal:  J Org Chem       Date:  2009-02-06       Impact factor: 4.354

10.  Design, synthesis, and biological evaluation of platensimycin analogues with varying degrees of molecular complexity.

Authors:  K C Nicolaou; Antonia F Stepan; Troy Lister; Ang Li; Ana Montero; G Scott Tria; Craig I Turner; Yefeng Tang; Jianhua Wang; Ross M Denton; David J Edmonds
Journal:  J Am Chem Soc       Date:  2008-09-05       Impact factor: 15.419
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