Welcome to my research group web pages. Here you can find our more information about my research group and get an overview of the kind of projects that we are currently working on. For undergraduates, you can find out how to access all of my teaching materials and resources from the 'Teaching' tab, above. There are also plenty of links to resources that we have found to be useful from all over the world, and for group members, there are many more resources, such as electronic access to theses and to our group wiki. If you require anymore information, then do not hesitate to contact me directly.

15th August

15th August

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.