Stereoselectivity in the electrophilic addition reactions of stigmast-22(23)-ene derivatives |
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Authors: | M. Nakane M. Morisaki N. Ikekawa |
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Affiliation: | Laboratory of Chemistry for Natural Products, Tokyo Institute of Technology, Meguro-ku, Tokyo, Japan |
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Abstract: | Oxidation of 5α-stigmast-22-en-3- one (1) with m-chloroperbenzoic acid afforded [22R,23R]-epoxide 3 and [22S, 23S]-epoxide 2, in a 5:3 ratio. Reaction of 1 with iodine/silver acetate gave a mixture of iodoacetates 8 and 9, which on treatment with base yielded the single epoxide 2. Those results suggest that electrophiles may preferentially approach the Δ22-bond from the side of the 21-Me group, in accordance with observations with the ergosterol-like side chain. |
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