In a project aimed at the further development of the potent steroidal anti‐inflammatory Δ24‐dehydrocholesterol reductase (DHCR24) inhibitor SH‐42 we worked out routes to ring B seco‐steroidal analogues. The required building blocks, bearing rings C and D of the parent steroidal structure, were synthesised starting from ergocalciferol. The novel seco‐analogues carry aromatic residues as ring A equivalents at C‐4 position with variation of the linker length resulting in 4‐aryl‐, 4‐benzyl‐ and 4‐(arylethyl)perhydroindanes. As saturated analogues of the latter 4‐(cyclohexylethyl)perhydroindanes were prepared. Moreover, aromatic and aliphatic residues were attached to C‐5 position of the perhydroindane scaffold. Unfortunately, none of these structurally diverse seco‐analogues of SH‐42 showed noteworthy inhibition of target enzyme DHCR24, indicating the relevance of the intact steroidal structure for the development of potent inhibitors of this enzyme.