Homogeranic acid (1) and methyl geranylacetoacetate (18) were cyclized with bromine in the presence of silver fluoroborate to the brominated bicyclic compounds 2 and 19, respectively. Proton initiated cyclization competed with the brominative cyclization and gave trans lactone 3 and enol ether 20, respectively. Acid-catalyzed cyclization of 1 to 3 and isomerization of 3 to the cis lactone 5 were investigated. Both 3 and 5 were converted to the natural product dihydroactinidiolide (14).
|Original language||English (US)|
|Number of pages||5|
|Journal||Journal of Organic Chemistry|
|State||Published - 1978|
ASJC Scopus subject areas
- Organic Chemistry