Modification of the butenyl-spinosyns utilizing cross-metathesis

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• 作者：John Daeuble ; Thomas C. Sparks ; Peter Johnson ; Paul R. Graupner
• 关键词：Spinosyns ; Natural Products ; Semi-synthesis ; Olefin cross-metathesis
• 刊名：Bioorganic and Medicinal Chemistry
• 出版年：2009
• 出版时间：15 June 2009
• 年：2009
• 卷：17
• 期：12
• 页码：4197-4205
• 全文大小：1121 K

文摘

The discovery of a strain of Saccharopolyspora sp. that produced a number of spinosyn analogs that had not before been seen gave an ideal opportunity for extending our knowledge of that SAR of these highly efficacious insecticides. In particular, these compounds contained a butenyl group connected to C-21 which in the regular spinosyns was substituted with a simple ethyl group. The double bond therefore gave us a handle to further modify this position allowing us to substitute different groups there. In this paper we show one of our approaches to this modification using olefin cross-metathesis. Even though the spinosyns were not highly efficient substrates for metathesis reactions, we were nevertheless successful in extending their chemistry accordingly.