Synthesis of a 2,9-dioxabicyclo[3.3.1]nonane via double intramolecular hetero-Michael addition: Entry to the F-G ring system of the azaspiracids

被引:71
作者
Aiguade, J [1 ]
Hao, JL [1 ]
Forsyth, CJ [1 ]
机构
[1] Univ Minnesota, Dept Chem, Minneapolis, MN 55455 USA
关键词
D O I
10.1021/ol015556l
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An effective approach to form a 1,3-disubstituted 2,9-dioxabicyclo[3.3.1]nonane system representing the core of the F and G rings (C28-C34) of the azaspiracid natural products has been developed, The double intramolecular hetero-Michael addition (DIHMA) of a diol upon an ynone generated the bicyclic ketal in a highly diastereoselective fashion.
引用
收藏
页码:979 / 982
页数:4
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