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Stereodivergent Approach to the Avermectins Based on “Super Silyl” Directed Aldol Reactions
Patrick B. Brady, Susumu Oda, and Hisashi Yamamoto
Org.Lett.2014, 16, 3864−3867
The avermectins, a series 16-membered macrocyclic lactone derivatives, have held a prominent place in polyketide-derived therapeutics. Meanwhile, the avermectins have become some of the most widely used anti-insecticides in crop protection. Due to their structural complexities, synthesis of the avermectins is challenging.
In this paper, a stereodivergent approach to the spiroketal fragment of the avermectins is developed based on the utilization of the tris(trimethylsilyl)silyl “super silyl” group directing three aldol reactions. Each of reaction would be manipulated to select for multiple stereochemical outcomes, thereby aﬀording 16 stereoisomers along the same linear skeleton. This concise route provides access to synthesis of avermectin A1a.