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A Novel Pentannulation Sequence. Facile Access to Key Intermediates for the Synthesis of Exaltone ® and Muscone
Author(s) -
Fehr Charles
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.19830660817
Subject(s) - chemistry , sulfonyl , toluene , potassium hydroxide , sulfoxide , yield (engineering) , sequence (biology) , bicyclic molecule , organic chemistry , potassium , dimethyl sulfoxide , medicinal chemistry , biochemistry , alkyl , materials science , metallurgy
Treatment of the sulfonyl ketones 1a and 1b with potassium t ‐butoxide in toluene or with potassium hydroxide in toluene/dimethyl sulfoxide affords in high yield the bicyclic dienes 3a and 3b , important precursors for Exaltone ® and (±)‐muscone. An application of this novel pentannulation sequence is demonstrated for the sulfonyl ketones 6, 10 , and 14 . An intermolecular variant is exemplified by the synthesis of diene 22 .