Literature DB >> 10750497

A novel, one-pot ring expansion of cyclobutanones. Syntheses of carbovir and aristeromycin.

B Brown1, L S Hegedus.   

Abstract

A novel, one-pot ring-expansion procedure was developed using Me3S(O)I, NaH, and Sc(OTf)3. The scope and limitations were briefly examined, and a tentative mechanism was proposed. Application of the methodology to known cyclobutanone 1 provided the corresponding cyclopentanone, which was successfully advanced to (+)-carbovir and (+)-aristeromycin.

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Year:  2000        PMID: 10750497     DOI: 10.1021/jo9919759

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  2 in total

1.  Synthesis of Unusually Strained Spiro Ring Systems and Their Exploits in Synthesis.

Authors:  Richard J Duffy; Kay A Morris; Daniel Romo
Journal:  Tetrahedron       Date:  2009-09-01       Impact factor: 2.457

2.  Enantioselective Synthesis of Vicinal All-Carbon Quaternary Centers via Iridium-Catalyzed Allylic Alkylation.

Authors:  J Caleb Hethcox; Samantha E Shockley; Brian M Stoltz
Journal:  Angew Chem Int Ed Engl       Date:  2018-06-11       Impact factor: 15.336

  2 in total

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