大环二萜天然产物(±)-Sinulariol-A的全合成

Total Synthesis of Natural Macrocyclic Diterpene (±)-Sinulariol-A

以香叶醇为起始原料 ,经多步反应完成了西松烷型大环二萜类天然产物 (± ) -Sinulariol-A的全合成 .合成的关键步骤是醛 5与丙烯酸甲酯经改进的

The total synthesis of natural macrocyclic diterpene (±)-Sinulariol-A(1), a marine cembraniol, starting from geraniol is described. The key steps are the chromium-induced intramolecular cyclization of the ω-formyl-β-methoxycarbonylallyl halide 9, the phosphine-catalyzed Morita-Baylis-Hillman addition of methyl acrylate to aldehyde 5 and chlorination reaction of ester 7. The 14-membered ring cis-hydroxy ester 10 was then underwent reduction with LiAlH 4 to produce the title compound(±)-1 in 85% yield.