Synthesis of (-)-Piperitylmagnolol Featuring ortho-Selective Deiodination and Pd-Catalyzed Allylation

Atsushi Ikoma, Narihito Ogawa, Daiki Kondo, Hiroki Kawada, Yuichi Kobayashi

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

A 1,4-addition strategy using an enone and a copper reagent was studied for the synthesis of (-)-piperitylmagnolol. A MOM-protected biphenol copper reagent was added to BF3·OEt2-activated 4-isopropylcyclohexenone, whereas 1,4-addition of protected monophenol reagents possessing an allyl group was found to be unsuccessful. The allyl group was later attached to the p-,p′-diiodo-biphenol ring by Pd-catalyzed coupling with allylborate. The aforementioned iodide was synthesized using a new method for ortho-selective deiodination of o-,p-diiodophenols.

Original languageEnglish
Pages (from-to)2074-2077
Number of pages4
JournalOrganic Letters
Volume18
Issue number9
DOIs
Publication statusPublished - 6 May 2016

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