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Remodeling of fumagillol: discovery of an oxygen-directed oxidative Mannich reaction.


ABSTRACT: 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.

SUBMITTER: Grenning AJ 

PROVIDER: S-EPMC3927640 | biostudies-literature |

REPOSITORIES: biostudies-literature

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