Observations Regarding the Regiochemical and Stereochemical Course of the Cyclization of Complex 5-Hexenyl Radicals: An Approach to Perhydronaphthalenes

Che-Ping Chuang, Judith C. Gallucci, David J. Hart, Christopher Hoffman

Research output: Contribution to journalArticle

24 Citations (Scopus)

Abstract

Iodo lactones 4 and 5 were prepared from m-anisic acid (10) and m-(isopropylthio)benzoic acid (15),respectively, by using a reductive alkylation-halolactonization-free radical cyclization sequence. Enones 6-9 were prepared from benzoic acid by way of acid chloride 30 by using a palladium-catalyzed coupling reaction. Tri-n-butyltin hydride mediated cyclization of 4-7 and 9 afforded substituted perhydronaphthalenes with good stereoselectivity. The radical derived from enone 8 gave perhydroindan 40. A transition-state geometry for the cyclization of enones 6-9 is proposed.

Original languageEnglish
Pages (from-to)3218-3226
Number of pages9
JournalJournal of Organic Chemistry
Volume53
Issue number14
DOIs
Publication statusPublished - 1988 Jun 1

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

Fingerprint Dive into the research topics of 'Observations Regarding the Regiochemical and Stereochemical Course of the Cyclization of Complex 5-Hexenyl Radicals: An Approach to Perhydronaphthalenes'. Together they form a unique fingerprint.

  • Cite this