Nature-like odorants by stereoselective ring enlargement of cyclohexanone and cyclododecanone

Article abstract of DOI:10.1016/0040-4020(96)00170-6

Both enantiomers of muscolide (3a/b), (R)-(-)-phoracantholide I [(R)-3c] and the homologous (9R)-(-)-9-tetradecanolide [(R)-3d) were synthesized by ring enlargement of cyclohexanone (6c) and cyclododecanone (6a). The ring-enlargement sequence was improved by oxidation of 9/10 with ruthenium tetroxide and reduction of 8 using catecholborane.