Synthesis and characterization of (±)-13-hydroxy-3,11-diaza steroids

An efficient strategy for introducing a nitrogen atom in positions 3 and 11 of the steroidal skeleton, which are key positions for biological purposes, is described. This procedure involves an intramolecular Diels–Alder cycloaddition of o-quinodimethanes which are generated from a 3-azabicyclo[4.2.0]octa-1,3,5-trien-7-one. The characteristic 1H and 13C NMR spectroscopic features of the synthesized compounds are reported.

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► Total synthesis of diheterosteroids possessing nitrogen atoms is described.
► Steroids matching ring fusion configuration of natural product are generated by a Diels–Alder cycloaddition.
► Functionalization of the lateral chain by a Wacker-type oxidation is possible.