Synthesis and stereochemistry of the terminal spiroketal domain of the phosphatase inhibitor dinophysistoxin-2

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• 作者：Craig J. Forsyth ; Ce Wang
• 关键词：Dinophysistoxin-II ; Phosphatase inhibitor ; Stereochemistry ; C35-configuration ; Synthesis ; Spiroketal
• 刊名：Bioorganic and Medicinal Chemistry Letters
• 出版年：2008
• 期刊代码：10_0960894x
• 类别：ch
• 出版时间：15 May 2008
• 卷：18
• 期：10
• 页码：3043-3046
• 文件大小：158 K

摘要

An expedient synthesis of both axially and equatorially C35 methyl substituted spiroketals representing the C28–C38 domain of the potent and selective protein serine/threonine phosphatase inhibitor dinophysistoxin-2 (DTX-2) was developed to enable comparative stereochemical analyses and a stereochemically correct total synthesis of DTX-2. Comparison of proton and carbon NMR data of the synthetic diastereomers with those published for DTX-2 indicates that DTX-2 possesses the (30S*,34R*,35S*)-relative configuration with an axial C35 methyl substituent.