Synthetic studies toward the C5-C20 domain of the azaspiracids

被引:51
作者
Dounay, AB [1 ]
Forsyth, CJ [1 ]
机构
[1] Univ Minnesota, Dept Chem, Minneapolis, MN 55455 USA
关键词
D O I
10.1021/ol015570y
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An approach toward the C5-C20 THF-fused trioxadispiroketal portion of the azaspiracids is reported. The highly substituted azaspiracid D ring (C16-C19) was prepared by the one-pot conversion of a tetraol into a tetrahydrofuran. Efforts to establish the C10 and C13 spiroketal centers via an oxonium-initiated bis-spiroketalization under both kinetic and thermodynamic conditions have yielded the (10R,13S)-trioxadispiroketal 19 as the major product, which is diastereomeric with the (10R*,13R*) relative configuration assigned to the azaspiracids.
引用
收藏
页码:975 / 978
页数:4
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