Ring-expanding enyne metathesis and progress towards the isodaucane sesquiterpenes
Rauschenberger, Blake Harold
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Enyne metathesis is a versatile reaction for carbon-carbon bond formation and is utilized for the synthesis of substituted 1,3-dienes. Ring-expanding enyne metathesis is an efficient method of constructing substituted cycloheptadienes from cyclopentenes. The reaction is studied in-depth in terms of substrate scope, mechanism and applications. Progress towards the total synthesis of a class of biologically active natural products, the Isodaucanes, by ring-expanding enyne metathesis is demonstrated. A novel, site-selective and stereoconvergent synthesis of complex adducts accomplished by a sequential cross enyne metathesis/cycloaddition reaction is presented, in which the products have future uses in ring-expanding enyne metathesis.