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Citation: ZHANG Cheng-Lu, SUN Chun-Li, HAN Fu-Zhong, LIU Lin. The Total Synthesis of Missourienol[J]. Chinese Journal of Applied Chemistry, ;2006, 23(8): 939-941. shu

The Total Synthesis of Missourienol

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

Corresponding author: ZHANG Cheng-Lu,
Received Date: 16 September 2005
Available Online: 1 March 2006

α-Cyclocitral(1) was used as the A-ring synthon and triphenyl phosphonium chloride(2) as the C-ring synthon,and the tricyclic structure of α,β-unsaturated ketone was constructed through the Birch reduction.Finally the target compound was synthesized by the reaction of i-PrMgBr,a Grignard reagent,with α,β-unsaturated ketone through neucleophilic addition under the catalysis of anhydrous CeCl₃.The IR absorption peak at 3 418 cm^-1 indicated that the hydroxyl group was introduced into the target compound successfully.In the ¹H NMR spectrum,the peaks at δ0.96,1.83 and 6.98 indicate that the iso-propyl group has been bonded to C-13 in the target compound.The ¹³C NMR and HRMS data were consistent with the structure of the target compound.In conclusion,the target compound was successfully synthesized through the method reported in this paper.
- tricyclic diterpene,
- total synthesis,
- missourienol
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