Rhodium(II) acetate-catalyzed O–H bond insertion in Maoecrystal V
Gong, J.; Lin, G.; Sun, W.; Li, C.-C.; Yang, Z. J. Am. Chem. Soc. 2010, 132, 16745-16746.
Please let this be a normal fieldtrip...
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Welcome, class!
Maoecrystal V, a compound found in Isodon plants, is selectively cytotoxic against human tumor cells. In 2010, Gong, J. and colleagues devised a complete synthesis of it (J. Am. Chem. Soc. 2010, 132, 16745-16746.). The reaction we shall explore today, from molecules 5 to 4, is one step in that synthesis! In it, rhodium(II) acetate catalyzes the insertion of an O–H bond into 5, which releases a diazo group and cyclizes the structure to afford 4. This compound then gives way to the remainder of the synthesis.
We shall explore this reaction in depth, carefully considering its mechanism, the protocol of Gong et al, and the nature of such rhodium-catalyzed reactions in general. Additionally, we will correlate the spectra data for molecule 4 and examine other relevant, current research.
Let's shrink to the molecular level and go!
