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Combining asymmetric catalysis with natural product functionalization through enantioselective alpha-fluorination.

ABSTRACT: An examination into the derivatization of various natural products using newly developed alpha-fluorination methodology is disclosed. An activated ketene enolate, generated from an acid chloride, is allowed to react with an electrophilic fluorine source (NFSi). Quenching the reaction with a nucleophilic natural product produces biologically relevant alpha-fluorinated carbonyl derivatives of select chemotherapeutics, antibiotics, and other pharmaceuticals.

SUBMITTER: Erb J

PROVIDER: S-EPMC3443555 | biostudies-literature | 2010 Feb

REPOSITORIES: biostudies-literature

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Combining asymmetric catalysis with natural product functionalization through enantioselective alpha-fluorination.

Erb Jeremy J Alden-Danforth Ethan E Kopf Nathan N Scerba Michael T MT Lectka Thomas T

The Journal of organic chemistry 20100201 3

An examination into the derivatization of various natural products using newly developed alpha-fluorination methodology is disclosed. An activated ketene enolate, generated from an acid chloride, is allowed to react with an electrophilic fluorine source (NFSi). Quenching the reaction with a nucleophilic natural product produces biologically relevant alpha-fluorinated carbonyl derivatives of select chemotherapeutics, antibiotics, and other pharmaceuticals. ...[more]

PMID: 20039641

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