Synthetic efforts toward the C22-C36 subunit of halichondrin B utilizing local and imposed symmetry
Synthetic efforts toward the C22-C36 subunit of halichondrin B utilizing local and imposed symmetry
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DOI：
10.1021/ol0473400
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发表时间：
2005-02-17
期刊：
影响因子：
5.2
通讯作者：
Burke, SD
中科院分区：
文献类型：
--
作者：
Keller, VA;Kim, L;Burke, SD
[图表]软海绵素 B 的 C22-C34 部分 (2) 由内消旋双甲硅烷基保护的环戊烯二醇 (7) 合成，分 20 个步骤，总产率为 7%。这是通过双向合成/末端分化策略实现的，该策略通过非手性、介观对称中间体进行八个步骤，并采用 Pd(0) 介导的不对称双环醚化来建立两个四氢吡喃环。
[GRAPHICS]The C22-C34 portion (2) of halichondrin B was synthesized from meso-symmetric bis-silyl protected cyclopentenediol (7) in 20 steps and 7% overall yield. This was accomplished through a two-directional synthesis/terminus differentiation strategy that proceeded via achiral, mesosymmetric intermediates for eight steps and employed a Pd(0)-mediated asymmetric double cycloetherification to establish both tetrahydropyran rings.