147. Model reactions for the biosynthesis of damascone-related compounds and their preparative application

Article abstract of DOI:10.1002/hlca.19730560507

We report a new general synthesis of damasconcs. In the presence of acids, 7, 8-dehydro-β-ionole (10) or the related diols 11 are converted into a mixture of β-damascone (2) and the 7, 8-dehydrotheaspiranes (19). In the same way the 6-hydroxy-7, 8-dehydro-α-ionoles 12 are transformed into a mixture of β-damascenone (3) and the 8-oxatheaspiranes (20). The reaction provides access to damascone derivatives 4-7 which have been found in nature. These synthetic experiments lend support to our hypotheses concerning the biogenesis of damascones from suitable carotenoids or their metabolites.