55.Total Synthesis of Drimane-Type Sesquiterpenoids Enabled by a Gold-Catalyzed Tandem Reaction

H. Shi, L. C. Fang, C. H. Tan, L. L. SHi, W. B. Zhang, C. C. Li*, T. P. Luo*, Z. Yang*

J. Am. Chem. Soc. 2011, 132, 14944

• Highlighted in Org. Chem. Highlights, August, 2012.

Development of a gold-catalyzed tandem reaction of 1,7-diynes with both internal and external nucleophiles was realized, which constructed five chemical bonds, two rings, and two stereogenic centers in a single step. Based on the novel cascade transformation, we achieved a unified strategy toward the stereoselective total syntheses of C-15 oxygenated drimane-type sesquiterpenoids and their analogues, which provided the natural products kuehneromycin A, antrocin, anhydromarasmone, and marasmene as a proof-of-concept study.

*This publication was highlighted on http://www.organic-chemistry.org/Highlights/2012/13August.shtm