Compounds 1 and 2 exhibit an oxetane ring (a four-membered
Chapter 8, Problem 8.89(choose chapter or problem)
Compounds 1 and 2 exhibit an oxetane ring (a four-membered ring containing an oxygen atom), which is a very important structural feature in a number of natural products. For example, an oxetane ring is present in the structure of taxol, used in the treatment of breast cancer. When either 1 or 2 is treated with TsCl and pyridine, followed by t-BuOK, the Zaitsev elimination product dominates, despite the use of a sterically hindered base (Tetrahedron Lett. 2007, 48, 83538355). Determine the stereochemical outcome for each of these processes and draw the expected product in each case. Use Newman projections to justify your answers. Ph OH O Ph OH 1 2 O
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