Efficient Rhodium-Catalyzed Conjugate Addition of Arylboronic Acids to Unsaturated Furano Esters for the Highly Stereoselective Synthesis of Four Natural Trisubstituted Furanolignans

被引：10

作者：

Mondiere, Aurelie ^{[1
]}

Pousse, Guillaume ^{[1
]}

Bouyssi, Didier ^{[1
]}

Balme, Genevieve ^{[1
]}

机构：

[1] Univ Lyon 1, ICBMS, CNRS, UMR 5246,ESCPE Lyon, F-69622 Villeurbanne, France

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 2009卷 / 25期

关键词：

Lignans; Rhodium; Conjugate addition; Boronic acids; Microwave chemistry; ELECTRON-DEFICIENT OLEFINS; DIPOLAR APROTIC MEDIA; ALPHA-CYANO ESTERS; BETA-KETO-ESTERS; ASYMMETRIC 1,4-ADDITION; ORGANOBORONIC ACIDS; MALONATE ESTERS; LIGNANS; NEOLIGNANS; ARYL;

D O I：

10.1002/ejoc.200900643

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Four natural lignans, (+/-)-dihydrosesamin (1a), (+/-)-lariciresinol methyl ether (1b), (+/-)-sanshodiol methyl ether (1c) and (+/-)-acuminatin methyl ether (1d), were prepared stereoselectively in five steps from a 4-(arylmethylene)-2-methoxy-tetrahydrofuran derivative obtained by a MCR reaction. The key step of this synthesis is the microwave-assisted stereoselective addition of a boronic acid (Hayashi-Miyaura reaction) to a 4-ethoxycarbonyldihydrofuran, generating three contiguous stereogenic centers with an excellent diastereoselectivity. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

引用

页码：4225 / 4229

页数：5

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