Open AccessRemodeling of Fumagillol: Discovery of an Oxygen-Directed Oxidative Mannich Reaction
Author(s) -
Alexander J. Grenning,
John K. Snyder,
John A. Porco
Publication year - 2014
Publication title -
organic letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.94
H-Index - 239
eISSN - 1523-7060
pISSN - 1523-7052
DOI - 10.1021/ol4035269
Subject(s) - chemistry , natural product , oxidative phosphorylation , combinatorial chemistry , mannich reaction , oxidative coupling of methane , drug discovery , organic chemistry , stereochemistry , biochemistry , catalysis
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.
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