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Construction of Large Carbocyclic Rings by Ireland‐Claisen Rearrangement of O ‐Silylated Lactone Enolates: Synthesis of (±)‐muscone
Author(s) -
Brunner Rudolf K.,
Borschberg HansJürg
Publication year - 1983
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19830660827
Subject(s) - chemistry , claisen rearrangement , yield (engineering) , lactone , stereochemistry , bicyclic molecule , metallurgy , materials science
(±)‐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) .