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

Grenning AJ, Snyder JK, Porco JA - Org. Lett. (2014)

Bottom Line: 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.

View Article: PubMed Central - PubMed

Affiliation: Center for Chemical Methodology and Library Development, Boston University , 590 Commonwealth Avenue, Boston, Massachusetts 02215, United States.

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.

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Deuterium Labeling Study
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sch6: Deuterium Labeling Study


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

Grenning AJ, Snyder JK, Porco JA - Org. Lett. (2014)

Deuterium Labeling Study
© Copyright Policy
Related In: Results  -  Collection

Show All Figures
getmorefigures.php?uid=PMC3927640&req=5

sch6: Deuterium Labeling Study
Bottom Line: 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.

View Article: PubMed Central - PubMed

Affiliation: Center for Chemical Methodology and Library Development, Boston University , 590 Commonwealth Avenue, Boston, Massachusetts 02215, United States.

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.

Show MeSH