Tamaru reaction-based approach towards the synthesis of muscone and analogues using renewable sources

Abstract

Muscone is considered as the king of fragrances, due to its rare occurrence and exotic nature, many attempts have been made to synthesise musk analogues. The presence of methyl group at the C-3 position from ketone imparts the musk character to the molecule. The Tamaru reaction (Ni-catalysed reductive coupling of aldehyde and 1,3-dienes) is used as the key step for the installation of the methyl group in an efficient manner to afford the RCM precursor diene. A short three step sequence involving oxidation, RCM and reduction gave a highly efficient access to muscone and analogues. Both the precursors, namely, the aldehyde and isoprene are derived from renewable resource.