Premium
β‐Cleavage of Bis(homoallylic) Potassium Alkoxides. Synthesis of γ‐damascone
Author(s) -
Snowden Roger L.,
Linder Simon M.
Publication year - 1988
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.19880710702
Subject(s) - chemistry , alkoxide , potassium , cleavage (geology) , transformation (genetics) , stereochemistry , organic chemistry , catalysis , geotechnical engineering , fracture (geology) , engineering , biochemistry , gene
Abstract Starting from the γ‐lactone cis ‐ 1 , two new syntheses of γ‐damascone (( E )‐ 4 ) are described. In both syntheses, the key step involves the β‐cleavage of a bis(homoallylic) potassium alkoxide, viz. the transformation of 3a to 20 and ( E / Z )‐ 4 , and the conversion of 21a to 23 and ( E / Z )‐ 24 .