Total synthesis of taxane terpenes: cyclase phase

详细信息    查看全文

• 作者：Yoshihiro Ishihara<sup>&dagger ; sup> ; Abraham Mendoza<sup>&dagger ; sup> ; Phil S. Baran<sup> ; sup><sup>pbaran@scripps.edusup>
• 关键词：Total synthesis ; Terpene ; Taxane ; Taxadiene ; Cyclase phase
• 刊名：Tetrahedron
• 出版年：2013
• 出版时间：8 July, 2013
• 年：2013
• 卷：69
• 期：27-28
• 页码：5685-5701
• 全文大小：6701 K

文摘

A full account of synthetic efforts toward a lowly oxidized taxane framework is presented. A non-natural taxane, dubbed ¡®taxadienone¡¯, was synthesized as our first entry into the taxane family of diterpenes. The final synthetic sequence illustrates a seven-step, gram-scale, and enantioselective route to this tricyclic compound in 18 % overall yield. This product was then modified further to give (+)-taxadiene, the lowest oxidized member of the taxane family of natural products.