Concise total syntheses of the bioactive mesotricyclic diterpenoids jatrophatrione and citlalitrione

J Yang, YO Long, LA Paquette

Index: Yang, Jiong; Long, Yun Oliver; Paquette, Leo A. Journal of the American Chemical Society, 2003 , vol. 125, # 6 p. 1567 - 1574

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Citation Number: 39

Abstract

The highly functionalized [5.9. 5] tricyclic framework resident in jatrophatrione (1) and citlalitrione (2) has been synthesized. The route begins with the tandem anionic oxy-Cope rearrangement/methylation/transannular ene cyclization of 21 and subsequent introduction of a conjugated enone double bond. Hydroxyl-directed 1, 4-reduction of this functionality in 25 with LiAlH4/CuI/hexamethylphosphoramide/tetrahydrofuran sets the stage for the ...