Synthesis of new di- and triamine diosgenin dimers

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.

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