Ring-Construction/Stereoselective Functionalization Cascade: Total Synthesis of Pachastrissamine (Jaspine B) through Palladium-Catalyzed Bis-cyclization of Bromoallenes
Ring-Construction/Stereoselective Functionalization Cascade: Total Synthesis of Pachastrissamine (Jaspine B) through Palladium-Catalyzed Bis-cyclization of Bromoallenes
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DOI：
10.1021/ol901904w
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发表时间：
2009-10-01
期刊：
影响因子：
5.2
通讯作者：
Ohno, Hiroaki
中科院分区：
文献类型：
--
作者：
Inuki, Shinsuke;Yoshimitsu, Yuji;Ohno, Hiroaki
钯 (O) 催化的带有羟基和苯甲酰胺基团作为内部亲核试剂的溴联烯的环化立体选择性地提供官能化的四氢呋喃。以此双环化为关键步骤，实现了具有生物活性的海洋天然产物pachastrsamine的短全合成。
Palladium(O)-catalyzed cyclization of bromoallenes bearing hydroxyl and benzamide groups as internal nucleophiles stereoselectively provides functionalized tetrahydrofuran. With this bis-cyclization as the key step, a short total synthesis of pachastrissamine, a biologically active marine natural product, was achieved.