Alkynyliodonium salts in organic synthesis. Application to the total synthesis of (-)-agelastatin A and (-)-agelastatin B
Alkynyliodonium salts in organic synthesis. Application to the total synthesis of (-)-agelastatin A and (-)-agelastatin B
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DOI：
10.1021/ja027121e
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发表时间：
2002-08-07
影响因子：
15
通讯作者：
Saunders, JC
中科院分区：
文献类型：
--
作者：
Feldman, KS;Saunders, JC
以(R)-环氧氯丙烷为原料，分别用14步合成了(−)-agelastatin A和(−)-agelastatin B。两个序列的关键转化是亚硫酸盐促进的炔基碘鎓盐的环化，以提供关键的功能化环戊烯中间体。根据条件的不同，最后一步的选择性溴化反应会生成agelastatin A或agelastatin B。
The asymmetric total syntheses of (−)-agelastatin A and (−)-agelastatin B were accomplished in 14 steps each from (R)-epichlorohydrin. The pivotal transformation in both sequences was a sulfinate-promoted cyclization of an alkynyliodonium salt to furnish a key functionalized cyclopentene intermediate. Selective bromination in the final step led to either agelastatin A or agelastatin B, depending upon conditions.