Site-Selective Hydroxylation of Steroids via Oxometalloporphinates Covalently Linked to Ring D: Introduction of Hydroxyl Groups into the C(9) and C(12) Position of 5α-Androstanes

Article abstract of DOI:10.1021/jo00009a006

Oxidation of synthetic manganese(III) porphyrins attached to steroidal substrates at C(17) (cf. 2 and 3) gives rise to hydrogen atom abstraction at C(9) and/or C(12), thereby leading to hydroxyl incorporation at these sites.The use of more robust metalloporphyrins (cf. 9) results in substantial increases in the yields of hydroxylated 5α-androstanes.