AI Article Synopsis
- The study focuses on the use of alpha-halo-alpha-heteroarylalkyllithiums to create epoxides and aziridines when reacted with steroids containing C=O or C=NR groups.
- The reactions show regio- and stereoselectivity, specifically forming products at C-17 or C-20 positions of the steroids, with C-20(R) stereoisomer often being the primary isolate.
- To protect the hydroxyl groups on the steroids during the reactions, derivatization methods involving acetyl, ether, or lactone were utilized.
Article Abstract
Alpha-halo-alpha-heteroarylalkyllithiums, generated by deprotonation of the corresponding halides, when added promptly to steroids with C=O or C=NR groups, lead to epoxides and aziridines. The reactions are regio- and stereoselective; in fact, in the presence of more than one C=O group, the oxido or aziridino functions are formed uniquely at the C=O of C-17 (or C-20 depending on its position in the starting molecule), and the C-20(R) stereoisomer is often the only product isolated. Protection of the hydroxyl group present on several considered steroids was required, and it was accomplished through derivatization in acetyl, ether, or lactone.
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| http://dx.doi.org/10.1016/s0039-128x(02)00032-6 | DOI Listing |
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