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

被引：10

作者：

Ikoma, Atsushi ^{[1
]}

Ogawa, Narihito ^{[1
]}

Kondo, Daiki ^{[1
]}

Kawada, Hiroki ^{[1
]}

Kobayashi, Yuichi ^{[1
]}

机构：

[1] Tokyo Inst Technol, Dept Bioengn, Midori Ku, Box B-52,Nagatsuta Cho 4259, Yokohama, Kanagawa 2268501, Japan

来源：

ORGANIC LETTERS | 2016年 / 18卷 / 09期

关键词：

MAGNOLIA-OFFICINALIS; DIMETHYLBORON BROMIDE; ENOL PHOSPHATES; IODINATION; NEOLIGNANS; PHENOLS; HALIDES; MILD; CONVENIENT; INHIBITORS;

D O I：

10.1021/acs.orglett.6b00706

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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 center dot 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.

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收藏

页码：2074 / 2077

页数：4

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