A biomimetic synthesis of sacculatane diterpenoids.

The biomimetic synthesis of sacculatane-type epimeric compounds 14a and 14b is reported. The key synthetic step is the low-temperature superacidic cyclization of (all-E)-omega-acetoxygeranylgeraniol 12 obtained in nine steps from geranyllinalool (13). The 19-acetoxysacculata-7,17-dien-11-ol (14a) could be an important and convenient starting compound for the synthesis of other sacculatane diterpenoids.