Synthesis of new di- and triamine diosgenin dimers

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• 作者：Khaled Q. Shawakfeh ; Naim H. Al-Said ; Eman K. Abboushi
• 关键词：Dimer ; Aldehyde ; Diamine ; Reductive ; Amination ; Spacer
• 刊名：Tetrahedron
• 出版年：2010
• 出版时间：6 February 2010
• 年：2010
• 卷：66
• 期：6
• 页码：1420-1423
• 全文大小：190 K

文摘

In this study, a high yield synthesis of symmetrical steroidal polyamine dimers was achieved by the dimerization of (25R)-3β-acetoxyfurost-5-en-26-al via several di- and triamine linkers under mild conditions. To ensure the dimerization via E-E ring, the hydroxyl group in diosgenin was protected by an acetyl group. The important step is opening the spiroketal moiety using NaCNBH₃/AcOH to furnish the primary alcohol at C-26, followed by oxidation using PCC/CH₂Cl₂ to synthesize the desired aldehyde. Finally, reductive amination with diaminopropane, diaminobutane, diaminohexane, and spermidine using Na(OAc)₃BH as reducing agent, afforded the required four dimers.