Boron-Zinc Exchange in The Diastereoselective Arylation of Sugar-Based Aldehydes: Stereoselective Synthesis of (+)-7-epi-Goniofufurone and Analogues

被引：18

作者：

Wouters, Ana D. ^{[1
,2
]}

Bessa, Adrieli B. ^{[1
]}

Sachini, Maraisa ^{[3
]}

Wessjohann, Ludger A. ^{[2
]}

Luedtke, Diogo S. ^{[1
,3
]}

机构：

[1] Univ Sao Paulo, Fac Ciencias Farmaceut, BR-05508900 Sao Paulo, Brazil

[2] Leibniz Inst Plant Biochem, D-06120 Halle, Saale, Germany

[3] Univ Fed Rio Grande do Sul, Inst Quim, BR-91501970 Porto Alegre, RS, Brazil

来源：

SYNTHESIS-STUTTGART | 2013年 / 45卷 / 16期

基金：

巴西圣保罗研究基金会;

关键词：

arylzinc reagents; boron-zinc exchange; diastereoselective addition; chelation control; styryllactones; ASYMMETRIC ARYL TRANSFER; HIGHLY ENANTIOSELECTIVE ADDITION; ORGANOZINC REAGENTS; GRIGNARD-REAGENTS; STYRYL LACTONES; TITANIUM(IV) CATALYST; BENZYL HALIDES; KETONES; ALCOHOLS; EFFICIENT;

D O I：

10.1055/s-0033-1339285

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The substrate-controlled diastereoselective arylation of chiral aldehydes readily available from carbohydrates is described, using the boron-zinc exchange reaction to generate the transferable aryl groups. The methodology developed was applied to the total synthesis of the styryllactone (+)-7-epi-goniofufurone and analogues thereof.

引用

页码：2222 / 2233

页数：12

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