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Synthesis of marine alkaloids leucettamines B and C by beta-lactam ring rearrangement

A new method for the synthesis of marine alkaloids leucettamines B and C from Leucetta sp. sponges is described. The key step is the base-promoted rearrangement of β-lactam into imidazolone ring. Leucettamines B and C as well as their N-benzoyl derivatives were obtained in high yields. Single-crystal structures of both leucettamines B and C were determined by X-ray diffraction confirming Z-configuration of double bond at 4-position of imidazolone.

2-aminoimidazolone, β-lactam, marine alkaloids, transformation

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