Synthesis of the zoanthamine ABC ring system: Some surprises from intramolecular Diels-Alder reactions

被引:16
作者
Juhl, M [1 ]
Nielsen, TE [1 ]
Le Quement, S [1 ]
Tanner, D [1 ]
机构
[1] Tech Univ Denmark, Dept Chem, DK-2800 Lyngby, Denmark
关键词
D O I
10.1021/jo0520691
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
In connection with the total synthesis of the marine alkaloids zoanthamine and norzoanthamine, an elaborate model study was conducted starting from (-)-carvone. In nine steps alkenyl iodides corresponding to the C-11-C-24 fragment of zoanthamine were obtained. The alkenyl iodides were coupled to various stannanes (C-6-C-10 fragment) via the Corey modification of the Stille reaction, affording a variety of Diels-Alder precursors. An interesting and highly unexpected cascade reaction sequence was observed during the screening of an intramolecular Diels-Alder reaction. generating a novel tetracyclic framework. A slight, modification in the Diels-Alder precursor allowed the desired cycloaddition to take place, giving the cycloadduct in 87% yield.
引用
收藏
页码:265 / 280
页数:16
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