Asymmetric synthesis of dipropionate stereotetrads and application towards the total synthesis of Aplyronine A
Abstract
A general methodology for the synthesis of all eight dipropionate stereotetrads is described. The methodology features substrate-directed diastereoselective epoxidations of dienylsulfones and novel syn and anti methylations of epoxyvinylsulfones. Application of the above methodology towards the synthesis of Aplyronine A is presented. Synthesis of carbon 5-20, carbon 21-27 and carbon 28-33 fragments is described. Also scalable syntheses of dienylsulfones 2.1 and 2.2, which are key synthons for the above chemistry, are described.
Degree
Ph.D.
Advisors
Fuchs, Purdue University.
Subject Area
Organic chemistry
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