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Dioxirane oxidation of 3β‐substituted Δ 5 ‐steroids
Author(s) -
Parish Edward J.,
Qiu Zhihai
Publication year - 2004
Publication title -
lipids
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.601
H-Index - 120
eISSN - 1558-9307
pISSN - 0024-4201
DOI - 10.1007/s11745-004-1300-9
Subject(s) - dioxirane , chemistry , oxidizing agent , ketone , catalysis , organic chemistry , medicinal chemistry
This article reviews the utility of dioxiranes in the oxidation of 3β‐substituted Δ 5 ‐sterols. Dioxiranes are the smallest cyclic peroxides that contain a carbon atom. They can be generated in situ from Oxone ® (2KHSO 5 ·KHSO 4 ·K 2 SO 4 ) and a ketone. Dioxiranes are versatile oxidizing agents. The most common reaction of dioxiranes is epoxidation, with nearly 1∶1 ratios of α/β isomer products in all cases. Δ 5 ‐steroids with different side chains were epoxidized by dioxiranes generated in situ from several commercially available ketones. Although ketones function as catalyst, they were used in about an equivalent amount or large excess to accelerate the reaction.