A Concise and Efficient Synthesis of Spiroketals - Application to the Synthesis of SPIKET-P and a Spiroketal from Bactrocera Species

作者：Tomas Loic; Bourdon Benjamin; Caille Jean Claude; Gueyrard David^*; Goekjian Peter G

来源：European Journal of Organic Chemistry, 2013, (5): 915-920.

DOI：10.1002/ejoc.201201199

• Synthetic methods
• Cyclization
• Olefination
• Spiro compounds
• Natural products
• Lactones
• Enol ethers

We report the synthesis of spiroketals by sequence of enol ether synthesis and cyclization. The enol ethers were prepared from lactones by a Julia olefination reaction, and the starting chiral lactone was prepared from an industrial intermediate. This route is a concise and efficient way to synthesize naturally occurring and biologically interesting spiroketals. We used this sequence for the preparation of SPIKET-P and a spiroketal from Bactrocera species.

• 出版日期2013-2