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

Brunner Rudolf K. | Zendy; Borschberg HansJürg | Zendy

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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) .

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