Remodeling of fumagillol: Discovery of an oxygen-directed oxidative mannich reaction

Alexander J. Grenning, John K. Snyder, John A. Porco

Research output: Contribution to journalArticlepeer-review

21 Scopus citations

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.

Original languageEnglish (US)
Pages (from-to)792-795
Number of pages4
JournalOrganic Letters
Volume16
Issue number3
DOIs
StatePublished - Feb 7 2014
Externally publishedYes

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