Synthesis of (L)-4-Fluorotryptophan

Authors

David Konas, Montclair State UniversityFollow
Drilona Seci, Montclair State University
Safa Tamimi, Montclair State University

Document Type

Article

Publication Date

1-1-2012

Journal / Book Title

Synthetic Communications

Abstract

A new synthesis of stereochemically pure (L)-4-fluorotryptophan [i.e., (2S)-4-fluorotryptophan] in seven steps from 4-fluoroindole is described. A key reaction in the synthetic strategy is a diastereoselective alkylation of the Schollkopf chiral auxiliary with a fluorinated electrophile. All reaction steps are efficient and proceed in at least 80% yield.

DOI

10.1080/00397911.2010.523154

Montclair State University Digital Commons Citation

Konas, David; Seci, Drilona; and Tamimi, Safa, "Synthesis of (L)-4-Fluorotryptophan" (2012). Department of Chemistry and Biochemistry Faculty Scholarship and Creative Works. 36.
https://digitalcommons.montclair.edu/chem-biochem-facpubs/36