A Formal Synthesis of the C1-C9 Fragment of Amphidinolide C Employing the Tamaru Reaction

被引：34

作者：

Paudyal, Mahesh P. ^{[1
]}

Rath, Nigam P. ^{[1
]}

Spilling, Christopher D. ^{[1
]}

机构：

[1] Univ Missouri St Louis, Dept Chem & Biochem, St Louis, MO 63121 USA

来源：

ORGANIC LETTERS | 2010年 / 12卷 / 13期

基金：

美国国家科学基金会;

关键词：

NICKEL-CATALYZED HOMOALLYLATION; STEREOSELECTIVE-SYNTHESIS; CROSS-METATHESIS; ABSOLUTE STEREOCHEMISTRY; DINOFLAGELLATE; ALDEHYDES; 1,3-DIENES; MACROLIDES; ESTERS; MODEL;

D O I：

10.1021/ol100959a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Homoallylation of aldehydes with isoprene and triethylborane catalyzed by Ni(acac)(2) gave hydroxyalkenes in good yield with excellent regio- and stereoselectivity. Cross metathesis of the hydroxyalkenes with methyl acrylate using second-generation Grubbs catalyst and copper(I) iodide afforded alpha,beta-unsaturated esters, which underwent cyclization in the presence of DBU to produce tetrahydrofurans with the correct relative configuration for the C1-C9 fragment of amphidinolides C, C2, and F.

引用

页码：2954 / 2957

页数：4

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