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Radical and palladium-catalyzed cyclizations to cyclobutenes: An entry to the BCD ring system of penitrem D

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

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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.

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Details

Item Type: Article
Status: Published
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Rivkin, A
Gonzalez-Lopez De Turiso, F
Nagashima, T
Curran, DPcurran@pitt.eduCURRAN
Date: 28 May 2004
Date Type: Publication
Journal or Publication Title: Journal of Organic Chemistry
Volume: 69
Number: 11
Page Range: 3719 - 3725
DOI or Unique Handle: 10.1021/jo049873s
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 0022-3263
MeSH Headings: Catalysis; Cyclization; Cyclobutanes--chemical synthesis; Free Radicals--chemistry; Kinetics; Models, Molecular; Molecular Structure; Mycotoxins--chemical synthesis; Palladium--chemistry
PubMed ID: 15153001
Date Deposited: 18 Oct 2013 17:52
Last Modified: 02 Feb 2019 15:59
URI: http://d-scholarship-dev.library.pitt.edu/id/eprint/19891

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