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Citation: ZHANG Cheng-Lu, ZOU Li-Wei, LIU Lin, HAN Fu-Zhong, NIU Ming-Ming. Semi-synthesis of Some Aromatic Tricyclic Diterpenes[J]. Chinese Journal of Applied Chemistry, ;2007, 24(4): 448-451. shu

Semi-synthesis of Some Aromatic Tricyclic Diterpenes

1.
Department of Chemistry, Liaoning Normal University, Dalian 116029

Corresponding author: ZHANG Cheng-Lu,
Received Date: 21 June 2006
Available Online: 21 November 2006

Five tricyclic diterpenes(compounds 2,3,4,5 and 6) were synthesized from(±)-13-methoxy-8,11,13-podocarpatriene(1) via a simple approach,in which the ethyl group of compound 2 was introduced via alkyl substitution reaction when compound 1 was treated with n-BuLi and then reacted with ethyl bromide at -78℃.The oxidation of compound 2 with CrO₃ afforded compound 3 at -78℃.Compound 1 was treated with n-BuLi,alkylated with i-propyl bromide and then oxidized by CrO₃-HOAc to afford ketone 4.Diketone 5 was obtained by farther oxidation of ketone 4 using Jones reagent.Compound 6 was obtained by the enolization of compound 5 with the mixture of t-BuOK and t-BuOH.¹H NMR,¹³C NMR,IR,MS(EI),HRMS and element analysis were used to confirm the structures of compounds 2~6,and the results are consistent with those in literature.In conclusion,the target compounds were successfully synthesized with the method in this paper.
- aromatic tricyclic diterpene,
- semisynthesis,
- (±)-Methoxypodocarpatriene
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