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Synthese makrocyclischer Ketone durch Ringerweiterung; ein neuer Weg zu(±)‐Muscon
Author(s) -
Bienz Stefan,
Hesse Manfred
Publication year - 1987
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.19870700820
Subject(s) - chemistry , azobisisobutyronitrile , ketone , ring (chemistry) , hydrolysis , organic chemistry , medicinal chemistry , stereochemistry , polymerization , polymer
Synthesis of Macrocyclic Ketones by Ring‐Enlargement Reactions; a New Path to (±)‐Muscone A new synthetic route to macrocyclic ketones is described. Starting from 2‐nitrocycloalkanones, the ring‐enlarged compounds of the type 4 and 5 were prepared in three steps. Reduction of the NO 2 group with Bu 3 SnH and azobisisobutyronitrile led in moderate yields to simple β‐keto‐esters which were quantitatively hydrolyzed and decarboxylated to the ketones of the type 8 and 9 . The interesting fragrances Exaltone ® ( 8a ) and (±)‐muscone ( 9a ) were prepared in this way in overall yields of 22 and 18%, respectively.