eprintid: 20453
rev_number: 16
userid: 1418
dir: disk0/00/02/04/53
datestamp: 2014-02-07 00:01:26
lastmod: 2019-02-02 15:58:19
status_changed: 2014-02-07 00:01:26
type: article
metadata_visibility: show
item_issues_count: 0
eprint_status: archive
creators_name: Rivkin, A
creators_name: Nagashima, T
creators_name: Curran, DP
creators_email: 
creators_email: 
creators_email: curran@pitt.edu
creators_id: 
creators_id: 
creators_id: CURRAN
title: Samarium(II) iodide mediated radical/polar crossover reactions of cyclobutenes. An efficient approach to the BCD ring system of the penitrems
ispublished: pub
divisions: sch_as_chemistry
full_text_status: public
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.
date: 2003-02-20
date_type: published
publication: Organic Letters
volume: 5
number: 4
pagerange: 419 - 422
refereed: TRUE
issn: 1523-7060
id_number: 10.1021/ol0272491
pmid: 12583733
mesh_headings: Alkaloids--chemical synthesis
mesh_headings: Cyclization
mesh_headings: Cyclobutanes--chemistry
mesh_headings: Free Radicals--chemistry
mesh_headings: Hydrocarbons, Cyclic--chemical synthesis
mesh_headings: Iodides--chemistry
mesh_headings: Mycotoxins--chemical synthesis
mesh_headings: Samarium--chemistry
chemical_names: Alkaloids
chemical_names: Cyclobutanes
chemical_names: Free Radicals
chemical_names: Hydrocarbons, Cyclic
chemical_names: Iodides
chemical_names: Mycotoxins
chemical_names: samarium diiodide
chemical_names: tremortin
chemical_names: Samarium
citation:   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     
document_url: http://d-scholarship-dev.library.pitt.edu/20453/1/licence.txt