Abstract
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) |
|---|---|
| Pages (from-to) | 3693-3697 |
| Number of pages | 5 |
| Journal | Journal of Organic Chemistry |
| Volume | 43 |
| Issue number | 19 |
| DOIs | |
| State | Published - 1978 |