Synthetic routes to pyrroloiminoquinone alkaloids. A direct synthesis of makaluvamine C

被引:38
作者
Kraus, GA [1 ]
Selvakumar, N [1 ]
机构
[1] Iowa State Univ Sci & Technol, Dept Chem, Ames, IA 50011 USA
关键词
D O I
10.1021/jo981547n
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Makaluvamine C is a pyrroloiminoquinone which has been isolated from marine sponges. This molecule has been synthesized in 13 steps from p-anisidine. The key steps in this synthesis include an intramolecular nucleophilic aromatic substitution mediated by potassium tert-butoxide, the selective reduction of a dinitro ester using catalytic hydrogenation, and the novel use of Fremy's salt to synthesize an iminoquinone from an amino phenol. The synthesis of makaluvamine C has been achieved from p-anisidine in 13.1% overall yield.
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页码:9846 / 9849
页数:4
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