Construction of Large Carbocyclic Rings by Ireland‐Claisen Rearrangement of O‐Silylated Lactone Enolates: Synthesis of (±)‐muscone

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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).