Mild transition metal oxidants appear to be a highly useful way to generate stabilized electron-deficient radicals. These radicals add to alkenes to produce new electron-rich radicals which can be further oxidatively functionalized. The generality of this synthetic protocol will be investigated with respect to oxidant types, oxidizable functional groups, and acceptor alkenes. Upon completion of sufficient model systems, the synthesis of several biologically active lignans will be conducted. Lignans represent a ubiquitous class of compounds with a wide variety of bioactivity and they have clinical uses ranging from cancer chemotherapy to antifungal to dermatological treatments. The present synthetic approach utilizes this novel radical cyclization method and should be particularly general in its application toward lignan synthesis. Synthetic approaches to antineoplastic lignans to the podophyllotoxin family (e.g. VP-16) and stegane family (e.g. steganacin) are described.
