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Efficient Synthesis of (−)‐( R )‐Muscone by Enantioselective Protonation
Author(s) -
Fehr Charles,
Galindo José,
Farris Iris,
Cuenca Ana
Publication year - 2004
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.200490157
Subject(s) - enantioselective synthesis , chemistry , protonation , ozonolysis , ketone , bicyclic molecule , stereochemistry , organic chemistry , catalysis , ion
A new synthesis of (−)‐( R )‐muscone (( R )‐ 1 ) by means of enantioselective protonation of a bicyclic ketone enolate as the key step (see 6 →( S )‐ 4 in Scheme 2 ) is presented. The C 15 macrocyclic system is obtained by ozonolysis ( Scheme 7 ).