New Aromatic Musk Odorants: Design and Synthesis

Article abstract of DOI:10.1002/hlca.19890720716

By appropriate structural modification of known musk odorants, new strong musk odorants have been discovered.Incorporation of supplementary CH3 or CH2 groups into the basic musk skeleton of type G only slightly modifies the global shape of the molecule but leads to densely packed structures of enhanced lipophilicity.For the consturction of these highly substituted 1,2,3,4-tetrahydrohaphthalenes, new annulation sequences (intramolecular mono- and dialkylations; see Schemes 3, 6, and 8) have been developed and, in certain cases, the design of the target molecules was dictated by both structure-activity-realationship and synthetic considerations (e. g. 46 and 47, Scheme 6).This work also presents an original solution to an analytical problem: the distinction between a C2- and a C_s-symmetrical aromatic hydrocarbon (viz. 71 and 72) by conversion into a complex.