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A Short Synthesis of (±)‐Muscone
Author(s) -
Rautenstrauch Valentin,
Snowden Roger L.,
Linder Simon M.
Publication year - 1990
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.19900730416
Subject(s) - chemistry , alkoxide , bicyclic molecule , intramolecular force , enone , lewis acids and bases , cleavage (geology) , potassium , stereochemistry , organic chemistry , catalysis , geotechnical engineering , fracture (geology) , engineering
(±)‐Muscone ((±)‐1) has been synthesised in three steps from 2‐(2′‐methylprop‐2′‐enyl)cyclododecan‐1‐one ( 2 ). The synthesis involves two key transformations: a Lewis ‐acid‐mediated intramolecular ene reaction ( 2→3 ) and the β‐cleavage of the bicyclic potassium alkoxide 3a′ to the macrocyclic enone ( Z )‐ 11 .
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