Remodeling of fumagillol: discovery of an oxygen-directed oxidative Mannich reaction
Grenning, Alexander J.
Snyder, John K.
Porco, John A.
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CitationAlexander J Grenning, John K Snyder, John A Porco. 2014. "Remodeling of fumagillol: discovery of an oxygen-directed oxidative Mannich reaction.." Org Lett, Volume 16, Issue 3, pp. 792 - 795.
An efficient, two-step construction of highly complex alkaloid-like compounds from the natural product fumagillol is described. This approach, which mimics a biosynthetic cyclase/oxidase sequence, allows for rapid and efficient structure elaboration of the basic fumagillol scaffold with a variety of readily available coupling partners. Mechanistic experiments leading to the discovery of an oxygen-directed oxidative Mannich reaction are also described.