Synthesis of C17-OH-north unit of ritterazine G via “Red-Ox” modifications of hecogenin acetate

• A concise synthesis of C17-OH-north unit of ritterazine G.
• Discovery of a novel method for steroidal E-ring opening.
• A highly efficient, stereoselective introduction of the C17-OH.

The C17-OH-north unit of ritterazine G was prepared in 13 steps from hecogenin acetate. This synthesis features a highly efficient and stereoselective introduction of the C17-OH via E-ring cleavage/F-ring formation, D-ring oxidation, and F-ring cleavage/E-ring formation.

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