Literature DB >> 17489601

An expedient enantioselective strategy for the oxatetracyclic core of platensimycin.

Krishna P Kaliappan1, Velayutham Ravikumar.   

Abstract

An enantioselective route for the synthesis of oxatetracyclic core of platensimycin is reported for the first time using a 5-exo-trig cyclization followed by intramolecular etherification as key reactions. The requisite dienynone for the radical cyclization is synthesized in eight steps from the Wieland-Miescher ketone employing a Claisen rearrangement.

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Year:  2007        PMID： 17489601     DOI： 10.1021/ol070848t

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


  8 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.  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

5.  A concise ring-expansion route to the compact core of platensimycin.

Authors:  Nicholas A McGrath; Emily S Bartlett; Satapanawat Sittihan; Jon T Njardarson
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

6.  Synthesis of the AB subunit of angelmicin B through a tandem alkoxy radical fragmentation-etherification sequence.

Authors:  Jialiang Li; Louis J Todaro; David R Mootoo
Journal:  Org Lett       Date:  2008-03-07       Impact factor: 6.005

Review 7.  The use of platensimycin and platencin to fight antibiotic resistance.

Authors:  Adil M Allahverdiyev; Melahat Bagirova; Emrah Sefik Abamor; Sezen Canim Ates; Rabia Cakir Koc; Meral Miraloglu; Serhat Elcicek; Serkan Yaman; Gokce Unal
Journal:  Infect Drug Resist       Date:  2013-09-18       Impact factor: 4.003

Review 8.  A Review on Platensimycin: A Selective FabF Inhibitor.

Authors:  Manik Das; Partha Sakha Ghosh; Kuntal Manna
Journal:  Int J Med Chem       Date:  2016-01-28
  8 in total

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