Reactivity of acyclic (pentadienyl)iron(1+) cations: Synthetic studies directed toward the frondosins

被引：5
作者：
Lee, Do W. [1 ]
Pandey, Rajesh K. [1 ]
Lindeman, Sergey [1 ]
Donaldson, William A. [1 ]
机构：
[1] Marquette Univ, Dept Chem, Milwaukee, WI 53233 USA
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2011年 / 9卷 / 22期
基金：
美国国家科学基金会;
关键词：
SESQUITERPENE HYDROQUINONE DERIVATIVES; ORGANOIRON METHODOLOGY; REARRANGEMENT; CYCLOPROPANES; INHIBITOR; LIPHAGAL; ANALOGS;
D O I：
10.1039/c1ob05720k
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A short, 4-step route to the scaffold of frondosin A and B is reported. The [1-methoxycarbonyl-5-(2',5'-dimethoxyphenyl)pentadienyl]Fe(CO)(3)(+) cation was prepared in two steps from (methyl 6-oxo-2,4-hexadienoate)Fe(CO)(3). Reaction of this cation with isopropenyl Grignard or cyclohexenyllithium reagents affords (2-alkenyl-5-aryl-1-methoxycarbonyl-3-pentene-1,5-diyl)Fe(CO)(3) along with other addition products. Oxidative decomplexation of these (pentenediyl)iron complexes, utilizing CuCl2, affords 6-aryl-3-methoxycarbonyl-1,4-cycloheptadienes via the presumed intermediacy of a cis-divinylcyclopropane.
引用
收藏
页码：7742 / 7747
页数：6
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