Dittami, James P.
The formation of novel complex ring systems is an important synthetic technique for natural product synthesis. It has previously been shown that photocyclization of aryl vinyl ethers and thioethers with a pendant alkene side chain can introduce two or three new fused rings in a single reaction. Studies with aryl vinyl sulfides suggested that the photocyclization proceeds via an ylide intermediate which undergoes a subsequent ene-like rearrangement involving an intramolecular hydrogen transfer. In order to determine the mechanism for this process, the hydrogen transfer was monitored using deuterium substitution. The photoprecursor was selectively deuterated at two potential hydrogen-donor locations. The final deuterium incorporation in the new ring was analyzed by proton and carbon-13 NMR.
Worcester Polytechnic Institute
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Chemistry and Biochemistry