Rapid stereoselective access to the tetracyclic core of puupehenone and related sponge metabolites using metal-free radical cyclisations of cyclohexenyl-substituted 3-bromochroman-4-ones
- 作者：Robin G. Pritchard ; Helen M. Sheldrake ; Isobel Z. Taylor ; Timothy W. Wallace
- 关键词：Sesquiterpene– ; phenol ; Merosesquiterpene ; Benzo[a]xanthene ; Puupehenone ; Radical cyclisation ; 6-endo-Trig ;
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- 刊名：Tetrahedron Letters
- 出版年：2008
- 期刊代码：109_00404039
- 类别：ch
- 出版时间：23 June 2008
- 卷：49
- 期：26
- 页码：4156-4159
- 文件大小：289 K
摘要
The tetracyclic nucleus of puupehenone, 15-oxopuupehenol and other sesquiterpene–phenol natural products can be assembled stereoselectively in three steps, the last of these being the 6-endo-trig cyclisation of an alpha-keto radical generated from a substituted 2-(2-cyclohexenyl)ethyl 3-bromo-4-chromanone under metal-free conditions.