Synthesis of (−)-Piperitylmagnolol Featuring ortho-Selective Deiodination and Pd-Catalyzed Allylation,Organic Letters

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Synthesis of (−)-Piperitylmagnolol Featuring ortho-Selective Deiodination and Pd-Catalyzed Allylation
Organic Letters ( IF 4.9 ) Pub Date : 2016-04-25 00:00:00 , DOI: 10.1021/acs.orglett.6b00706
Atsushi Ikoma ₁ , Narihito Ogawa ₁ , Daiki Kondo ₁ , Hiroki Kawada ₁ , Yuichi Kobayashi ₁

Affiliation

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.

中文翻译：

具有邻位选择性脱碘和Pd催化的烯丙基化的（-）-哌啶基厚朴酚的合成

研究了使用烯酮和铜试剂的1，4-加成策略，用于合成（-）-哌啶基厚朴酚。将MOM保护的双酚铜试剂添加到BF ₃ ·OEt ₂活化的4-异丙基环己烯酮中，而发现未成功添加1,4-具有烯丙基的保护单酚试剂。烯丙基随后通过Pd催化的与烯丙基硼酸酯的偶合而连接至p-，p′-二碘代-双酚环。上述碘化物使用新的方法，用于合成邻的脱碘-选择性ø - ，p -diiodophenols。

更新日期：2016-04-25

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