Synthesis of clionamine B, an autophagy stimulating aminosteroid isolated from the sponge Cliona celata.

Clionamine B (2), an aminosteroid isolated from the marine sponge Cliona celata, has been synthesized starting from the plant sapogenin tigogenin (5). A key step in the synsthesis is the stereoselective introduction of the C-20 alpha-hydroxyl substituent via oxidation of a gamma-lactone enolate with molecular oxygen. Synthetic clionamine B (2) strongly stimulated autophagy in human breast cancer MCF-7 cells.