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Samarium(II) iodide mediated radical/polar crossover reactions of cyclobutenes. An efficient approach to the BCD ring system of the penitrems

Rivkin, A and Nagashima, T and Curran, DP (2003) Samarium(II) iodide mediated radical/polar crossover reactions of cyclobutenes. An efficient approach to the BCD ring system of the penitrems. Organic Letters, 5 (4). 419 - 422. ISSN 1523-7060

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Abstract

(Matrix presented) Radical/polar crossover reactions of derivatives of 1-(2-cyclobutenyl)-2-(2-iodoaryl)ethanones with acetone promoted by samarium diiodide and HMPA provide 1-(1-hydroxy-1-methylethyl)-2,2a,4,8b-tetrahydro-1H-cyclobuta[a] naphthalen-3-one derivatives in about 50% isolated yield. This reaction shows promise for construction of the BCD ring fragment of the penitrems.


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Details

Item Type: Article
Status: Published
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Rivkin, A
Nagashima, T
Curran, DPcurran@pitt.eduCURRAN
Date: 20 February 2003
Date Type: Publication
Journal or Publication Title: Organic Letters
Volume: 5
Number: 4
Page Range: 419 - 422
DOI or Unique Handle: 10.1021/ol0272491
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 1523-7060
MeSH Headings: Alkaloids--chemical synthesis; Cyclization; Cyclobutanes--chemistry; Free Radicals--chemistry; Hydrocarbons, Cyclic--chemical synthesis; Iodides--chemistry; Mycotoxins--chemical synthesis; Samarium--chemistry
PubMed ID: 12583733
Date Deposited: 07 Feb 2014 00:01
Last Modified: 02 Feb 2019 15:58
URI: http://d-scholarship.pitt.edu/id/eprint/20453

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