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.
A biomimetic synthesis of sacculatane diterpenoids.
Castelluccio F;Cimino G
2008
Abstract
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.File in questo prodotto:
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