Abstract:
On the basis of comparing the chemical structures of the rare natural bioactive triterpene squalene that mainly exists in liver oil of deep-sea sharks, with turpentine that is a natural plentiful resource of monoterpene in China, followed by the present researches and literatures survey, a feasible route is creatively suggested to synthesize squalene from turpentine. This synthesis route consists of 9 main reaction steps, namely: turpentine oil (pinenes) → pinane → pinane hydrogen peroxide → pinaol → linalool → geranylacetone → nerolidol → farnesol → farnesyl bromide → squalene, in which the last two key reactions, namely the bromination of farnesol and the reductive coupling of farnesyl bromide were mainly studied in detail. The suggested synthesis route has been confirmed to be feasible. From the reproducible turpentine oil, the goal squalene has been synthesized. Status and key points of each reaction step in the synthesis route were briefly described.