In a Bamford-Stevens-Shapiro reaction, a sulfonylhydrazone (1) undergoes base-catalyzed
Chapter 20, Problem 20.91(choose chapter or problem)
In a Bamford-Stevens-Shapiro reaction, a sulfonylhydrazone (1) undergoes base-catalyzed decomposition to give a vinyl lithium species (2) which can then react with an electrophile, such as compound 3. This reaction was recently employed in the total synthesis of frondosin B, a marine natural product with potential application in cancer chemotherapy (Chem. Sci. 2010, 1, 3742). Formation of 2 is believed to occur via a process that is mechanistically analogous to the Wolff-Kishner reduction. Draw a plausible mechanism for the conversion of 1 to 2. N N H S R R R O O Li 1 2 3 O O O (+)-Frondosin B O t-BuLi (2 equiv)
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