α-Acylamino radical cyclizations: Application to the synthesis of a tetracyclic substructure of gelsemine

Joong Kwon Choi, Deok-Chan Ha, David J. Hart, Chih Shone Lee, Subban Ramesh, Shung Wu

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Abstract

Syntheses of gelsemine substructures 2 and 3 are described. Free-radical precursors 14, 18, 35, and 38 were prepared, and their behavior upon treatment with tri-n-butyltin hydride and AIBN was examined. The radical derived from 14 afforded reduction product 15, whereas the radicals derived from 18, 35, and 38 gave cyclization products 23, 37, and 39, respectively. Aspects of these free-radical cyclizations as well as the conversion of 23 and 37 to 2 and 3, respectively, are presented.

Original languageEnglish
Pages (from-to)279-290
Number of pages12
JournalJournal of Organic Chemistry
Volume54
Issue number2
Publication statusPublished - 1989 Dec 1
Externally publishedYes

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ASJC Scopus subject areas

  • Organic Chemistry

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