Literature DB >> 15136852

Total synthesis of (-)-dysibetaine via a nitrenium ion cyclization-dienone cleavage strategy.

Duncan J Wardrop1, Matthew S Burge.   

Abstract

The diastereoselective total synthesis of the marine natural product (-)-dysibetaine is reported. The key steps in this venture are i) a diastereoselective nitrenium ion spirocyclization, which serves to generate the pyrrolidinone ring and quaternary stereocenter of the target, and ii) use of the 2-methoxycyclohexa-2,5-dienone ring formed during cyclization as a masked 2-amino-1,3-dicarbonyl synthon.

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Year:  2004        PMID： 15136852     DOI： 10.1039/b403081h

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN： 1359-7345            Impact factor:   6.222


  9 in total

1.  Nitrenium ion azaspirocyclization-spirodienone cleavage: a new synthetic strategy for the stereocontrolled preparation of highly substituted lactams and N-hydroxy lactams.

Authors:  Duncan J Wardrop; Matthew S Burge
Journal:  J Org Chem       Date:  2005-12-09       Impact factor: 4.354

Review 2.  Chemistry of polyvalent iodine.

Authors:  Viktor V Zhdankin; Peter J Stang
Journal:  Chem Rev       Date:  2008-12       Impact factor: 60.622

3.  Nitrenium ion-mediated alkene bis-cyclofunctionalization: total synthesis of (-)-swainsonine.

Authors:  Duncan J Wardrop; Edward G Bowen
Journal:  Org Lett       Date:  2011-04-12       Impact factor: 6.005

4.  Benzimidazopurine nucleosides from N6-aryl adenosine derivatives by PhI(OAc)2-mediated C-N bond formation, no metal needed.

Authors:  Sakilam Satishkumar; Mahesh K Lakshman
Journal:  Chem Commun (Camb)       Date:  2017-02-14       Impact factor: 6.222

5.  Pd-catalyzed versus uncatalyzed, PhI(OAc)2-mediated cyclization reactions of N6-([1,1'-biaryl]-2-yl)adenine nucleosides.

Authors:  Sakilam Satishkumar; Suresh Poudapally; Prasanna K Vuram; Venkateshwarlu Gurram; Narender Pottabathini; Dellamol Sebastian; Lijia Yang; Padmanava Pradhan; Mahesh K Lakshman
Journal:  ChemCatChem       Date:  2017-10-24       Impact factor: 5.686

6.  Intramolecular oxamidation of unsaturated O-alkyl hydroxamates: a remarkably versatile entry to hydroxy lactams.

Authors:  Duncan J Wardrop; Edward G Bowen; Raymond E Forslund; Adam D Sussman; Samanthi L Weerasekera
Journal:  J Am Chem Soc       Date:  2010-02-03       Impact factor: 15.419

7.  When nucleoside chemistry met hypervalent iodine reagents.

Authors:  Mahesh K Lakshman; Barbara Zajc
Journal:  ARKIVOC       Date:  2017-12-21       Impact factor: 1.140

8.  Enantiomerically Enriched 1,2-P,N-Bidentate Ferrocenyl Ligands for 1,3-Dipolar Cycloaddition and Transfer Hydrogenation Reactions.

Authors:  Irina A Utepova; Polina O Serebrennikova; Marina S Streltsova; Alexandra A Musikhina; Tatiana G Fedorchenko; Oleg N Chupakhin; Andrey P Antonchick
Journal:  Molecules       Date:  2018-05-30       Impact factor: 4.411

Review 9.  Electrophilic Aminating Agents in Total Synthesis.

Authors:  Lauren G O'Neil; John F Bower
Journal:  Angew Chem Int Ed Engl       Date:  2021-08-06       Impact factor: 16.823
  9 in total

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