Construction of Large Carbocyclic Rings by Ireland-Claisen Rearrangement of O-Silylated Lactone Enolates: Synthesis of (±)-muscone |
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Authors: | Rudolf K Brunner Hans-Jürg Borschberg |
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Abstract: | (±)-Muscone (5) has been synthesized from methyl 13-(chloroformyl)tridecanoate (6) in nine steps in an overall yield of 24%. The key steps involve an efficient transformation of the readily accessible 14-hydroxy-15-methyl-15-hexadecenoic acid (9) into the tetradecanolide 1 and a subsequent Ireland-Claisen rearrangement of its triethylsilyl enolate 2 to a 8:1-mixture of the stereoisomeric 15-membered carbocycles 4 and 10 (Scheme 4). |
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