A facile asymmetric synthesis of (+)-eldanolide

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• 作者：Linglong Kong ; Zeyang Zhuang ; Qingshou Chen ; Haibing Deng ; Zhiyong Tang ; Xueshun Jia ; Yulin Li ; Hongbin Zhai
• 刊名：Tetrahedron: Asymmetry
• 出版年：2007
• 出版时间：12 March 2007
• 年：2007
• 卷：18
• 期：4
• 页码：451-454
• 全文大小：143 K

文摘

The monoterpenoid pheromone (+)-eldanolide, a long range sex attractant, has been synthesized in four steps from the chiral 2,3-epoxy alcohol 4 in 36 % overall yield. Our synthetic strategy features the formation of a 1,3-diol by regio- and stereoselective ring opening of 2,3-epoxy alcohol 4, an intermediate easily available from Sharpless asymmetric epoxidation. Other key steps include one carbon elongation, saponification, and lactonization. The present work constitutes a general method for the rapid synthesis of a number of related γ-lactone natural products.