eprintid: 19891
rev_number: 18
userid: 1418
dir: disk0/00/01/98/91
datestamp: 2013-10-18 17:52:09
lastmod: 2019-02-02 15:59:07
status_changed: 2013-10-18 17:52:09
type: article
metadata_visibility: show
item_issues_count: 0
eprint_status: archive
creators_name: Rivkin, A
creators_name: Gonzalez-Lopez De Turiso, F
creators_name: Nagashima, T
creators_name: Curran, DP
creators_email: 
creators_email: 
creators_email: 
creators_email: curran@pitt.edu
creators_id: 
creators_id: 
creators_id: 
creators_id: CURRAN
title: Radical and palladium-catalyzed cyclizations to cyclobutenes: An entry to the BCD ring system of penitrem D
ispublished: pub
divisions: sch_as_chemistry
full_text_status: public
abstract: A novel approach toward the synthesis of the BCD ring system of penitrem D is described. The strategy capitalizes on the fast cyclization rates of aryl radicals into cyclobutenes and allows access to a variety of fused tricyclic structures. Radical/polar crossover reactions of precursors 24-29 promoted by samarium diiodide in the presence of HMPA and acetone allow access to the fully functionalized BCD ring system of penitrem D. The stereochemical implications of these processes are evaluated, and a Pd-mediated cyclization approach toward the penitrems is also introduced.
date: 2004-05-28
date_type: published
publication: Journal of Organic Chemistry
volume: 69
number: 11
pagerange: 3719 - 3725
refereed: TRUE
issn: 0022-3263
id_number: 10.1021/jo049873s
pmid: 15153001
mesh_headings: Catalysis
mesh_headings: Cyclization
mesh_headings: Cyclobutanes--chemical synthesis
mesh_headings: Free Radicals--chemistry
mesh_headings: Kinetics
mesh_headings: Models, Molecular
mesh_headings: Molecular Structure
mesh_headings: Mycotoxins--chemical synthesis
mesh_headings: Palladium--chemistry
chemical_names: Cyclobutanes
chemical_names: Free Radicals
chemical_names: Mycotoxins
chemical_names: tremortin
chemical_names: Palladium
citation:   Rivkin, A and Gonzalez-Lopez De Turiso, F and Nagashima, T and Curran, DP  (2004) Radical and palladium-catalyzed cyclizations to cyclobutenes: An entry to the BCD ring system of penitrem D.  Journal of Organic Chemistry, 69 (11).  3719 - 3725.  ISSN 0022-3263     
document_url: http://d-scholarship-dev.library.pitt.edu/19891/1/licence.txt