Diastereoselective synthesis of 2,3,6-trisubstituted tetrahydropyran-4-ones via prins cyclizations of enecarbamates: A formal synthesis of (+)-ratjadone A

被引:113
作者
Cossey, KN [1 ]
Funk, RL [1 ]
机构
[1] Penn State Univ, Dept Chem, University Pk, PA 16802 USA
关键词
D O I
10.1021/ja046940r
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Enecarbamates are shown to be excellent terminating groups for Prins cyclizations. A noteworthy feature of this methodology is the easy, stereoselective construction of the cyclization precursors by alkylation of metalated (E)-enecarbamates with epoxides. The stereochemistry of the resultant trisubstituted (E)-enecarbamates is then transferred with high fidelity to afford the frequently observed and biologically significant all-cis-2,3,6-trisubstituted tetrahydropyran substructures of naturally occurring compounds. Other substituted tetrahydropyrans, including 2,3,5,6-tetrasubstituted, cis-2,3-disubstituted, and cis-2,6-disubstituted, are also accessible. This methodology facilitated an exceptionally concise formal total synthesis of the nuclear export inhibitor (+)-ratjadone A. Copyright © 2004 American Chemical Society.
引用
收藏
页码:12216 / 12217
页数:2
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