New aromatic musk odorants: Design and synthesis

By appropriate structural modification of known musk odorants, new strong musk odorants have been discovered. Incorporation of supplementary CH 3 or CH 2 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 construction of these highly substituted 1,2,3,4‐tetrahydronaphthalenes, 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‐relationship 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 C 2 ‐ and a C s ‐symmetrical aromatic hydrocarbon ( viz. 71 and 72 ) by conversion into a [Cr(CO) 3 arene]complex.