Abstract
Abstract Photochemically generated singlet oxygen adds selectively to C20–C22 rather than C5–C6 double bond of pseudodiosgenin diacetate 1 to give diosone 4, an important intermediate for preparation of many steroidal drugs, and ene product 3 at room temperature. 3 was separated and characterized by 1H and 13C NMR as well as IR. When pyridine and acetic anhydride were presented, the Criegee rearrangement of 3 can yield 4, as a result, leading to a high collection yield (80% in acetonitrile) of 4.
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