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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
A concise effective deprotection of spiro 3-cyclic thiaza ketal of steroidal 1,4-dien-3-one
Bei Na Zhang1, Ying Chen, Qian Zhang
1Department of Medicinal Chemistry, Pharmacy School, Fudan University, Yi Xue Yuan Road 138, Shanghai 200032, China.
Abstract:
An effective deprotective method of spiro 3-cyclic thiaza ketal of steroidal 1,4-dien-3-ones using alkyl vinyl ether in the presence of protic acid followed by the treatment of aqueous alkali was described. This novel protocol could be fulfilled under mild condition with high yield. The mechanism mediated by a carbonium ion formed in situ was clarified by the capture of the cleaved fragment.
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