Department of Chemistry , University of Utah , 315 S 1400 E , Salt Lake City , Utah 84112 , United States.
Org Lett. 2019 Oct 4;21(19):7999-8002. doi: 10.1021/acs.orglett.9b02986. Epub 2019 Sep 25.
The bis-guanidinium ion family of natural products are revered for their utility in the study of ion channel physiology. While many congeners have been isolated with various oxidation and sulfation patterns, only two members of this family have been isolated bearing a carbon-carbon bond at C11, namely 11-saxitoxinethanoic acid and zetekitoxin AB. Herein we described a synthetic platform capable of efficiently targeting (+)-saxitoxin and 11-saxitoxinethanoic acid with an embedded C11 carbon-carbon bond. We demonstrate that this strategy enables direct enolate coupling in both an inter- and intramolecular fashion to create the C11-C15 carbon-carbon bond.
双胍离子家族的天然产物因其在离子通道生理学研究中的应用而备受推崇。虽然已经分离出许多具有不同氧化和硫酸化模式的同系物，但只有两种家族成员在 C11 处具有碳-碳键，即 11-脱毒甲藻氨酸和泽特基托毒素 AB。本文描述了一个能够高效靶向 (+)-石房蛤毒素和 11-脱毒甲藻氨酸并嵌入 C11 碳-碳键的合成平台。我们证明，该策略能够以分子内和分子间两种方式实现烯醇化物偶联，从而构建 C11-C15 碳-碳键。
