Synthesis of the C8-C20 and C21-C30 segments of pectenotoxin 2
Synthesis of the C8-C20 and C21-C30 segments of pectenotoxin 2
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DOI：
10.1016/j.tetlet.2007.04.136
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发表时间：
2007-06-25
影响因子：
1.8
通讯作者：
Suzuki, Takanori
中科院分区：
文献类型：
--
作者：
Fujiwara, Kenshu;Aki, Yu-ichi;Suzuki, Takanori
在本研究中，我们合成了腹泻性贝类毒素果胶毒素 2 的 C8-C20 和 C21-C30 片段。C8C20 片段由对应于 C8-C15 片段的膦酸酯（由 L-苹果酸经过 19 个步骤制备）和对应于 C16-C20 片段的醛（由 3-甲基-3-丁烯醇经过 9 个步骤合成）组装而成。十二步过程，包括 Homer-Wadsworth-Emmons 反应、所得烯酮的区域选择性和立体选择性还原、非对映选择性环氧化以及形成 C 环的 5-exo 环氧化物裂解。 C21-C30 片段是由 (S)-缩水甘油通过 5-外环氧化物裂解形成 E 环以及通过 Evans 方法在 C27 上进行立体选择性甲基化的途径，通过 13 个步骤构建的。 (c) 2007 Elsevier Ltd. 保留所有权利。
In this study, we synthesized the C8-C20 and C21-C30 segments of the diarrhetic shellfish toxin pectenotoxin 2. The C8C20 segment was assembled from a phosphonate corresponding to the C8-C15 segment (prepared from L-malic acid in 19 steps) and an aldehyde corresponding to the C16-C20 segment (synthesized from 3-methyl-3-butenol in nine steps) by a twelve-step process including the Homer-Wadsworth-Emmons reaction, regio- and stereoselective reduction of the resulting enone, diastereoselective epoxidation, and 5-exo epoxide cleavage forming the C-ring. The C21-C30 segment was constructed in 13 steps from (S)-glycidol via a route involving E-ring formation by 5-exo epoxide cleavage and stereoselective methylation at C27 by the Evans method. (c) 2007 Elsevier Ltd. All rights reserved.