Synthesis of new di- and triamine diosgenin dimers |
| |
Authors: | Khaled Q Shawakfeh Naim H Al-Said Eman K Abboushi |
| |
Institution: | Department of Applied Chemical Sciences, Jordan University of Science and Technology, PO Box 3030, Irbid 22110, Jordan |
| |
Abstract: | 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. |
| |
Keywords: | Dimer Aldehyde Diamine Reductive Amination Spacer |
本文献已被 ScienceDirect 等数据库收录! |
|