An efficient C-H oxidation protocol for alpha-hydroxylation of cyclic steroidal ethers.
[reaction: see text] Various C-16 hydroxy steroids have been prepared with the aid of CrO(3)/Bu(4)NIO(4). Out of the two possible reaction courses, transition state B is favored because of less steric interference between substrate and CrO(4). Thus, C-H bonds at C-16 are oxidized selectively.
Lee
Seongmin
S
Department of Chemistry, Purdue University, West Lafayette, Indiana 47907, USA.
Fuchs
Philip L
PL
D004583:Electrons; D004988:Ethers, Cyclic / Q000138:chemical synthesis*; D006900:Hydroxylation; D008968:Molecular Conformation; D010084:Oxidation-Reduction; D013141:Spiro Compounds / Q000138:chemical synthesis / Q000737:chemistry; D013256:Steroids / Q000138:chemical synthesis* / Q000737:chemistry
D004988:Ethers, Cyclic; D013141:Spiro Compounds; D013256:Steroids