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Round trip radical reactions from acyclic precursors to tricyclo[5.3.1.0<sup>2,6</sup>]undecanes. A new cascade radical cyclization approach to (±)-isogymnomitrene and (±)-gymnomitrene

Haney, BP and Curran, DP (2000) Round trip radical reactions from acyclic precursors to tricyclo[5.3.1.0<sup>2,6</sup>]undecanes. A new cascade radical cyclization approach to (±)-isogymnomitrene and (±)-gymnomitrene. Journal of Organic Chemistry, 65 (7). 2007 - 2013. ISSN 0022-3263

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Abstract

The synthesis and 'round trip radical cyclization' of 11-iodo-2,7,11- trimethyldodec-6-en-5-one are described. The round trip cyclization is a sequence of 5-exo, 6-endo, and 5-exo cyclizations in which the last radical cyclization occurs at the same carbon atom as the initial radical generation. The key second (6-endo) cyclization produces two stereoisomers, one of which cyclizes efficiently to isogymnomitrene ketone, while the other cyclizes inefficiently to gymnomitrene ketone. Efforts to influence the kinetic or thermodynamic outcome of the second cyclization were not successful, and the results are contrasted with a related cyclization of Jung and Rayle where thermodynamic control was readily established.


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Details

Item Type: Article
Status: Published
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Haney, BP
Curran, DPcurran@pitt.eduCURRAN
Date: 7 April 2000
Date Type: Publication
Journal or Publication Title: Journal of Organic Chemistry
Volume: 65
Number: 7
Page Range: 2007 - 2013
DOI or Unique Handle: 10.1021/jo9914871
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 0022-3263
MeSH Headings: Bridged Compounds--chemical synthesis; Cyclization; Free Radicals--chemistry; Stereoisomerism
PubMed ID: 10841670
Date Deposited: 21 Feb 2014 21:03
Last Modified: 02 Feb 2019 15:58
URI: http://d-scholarship.pitt.edu/id/eprint/20619

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