Title

The Dibromination of Homogentisic Acid Lactone

Document Type

Oral Presentation

Location

SURC Ballroom C/D

Start Date

15-5-2014

End Date

15-5-2014

Keywords

Natural Synthesis, Bromination, Optimization

Abstract

The recently described total synthetic pathway to clavatadine A, beneficial for its properties as an anticoagulant, is hindered by a step involving the dibromination of homogentisic acid lactone. This step produces moderate yields and mixed products preventing the discovered pathway from being practical in industrial production. Consequently, the efficiency of the dibromination step will be improved so that it results in at least an 80 percent yield and in a single product. In developing this alternative route many variables have been manipulated including the bromine source, base type, and reaction conditions. This work has revealed that the brominating agent N-bromosuccinimide, the bases pyridine, lithium acetate, potassium acetate, imidazole, and N,N-diisopropylethylamine, along with the solvents acetonitrile and tetrahydrofuran, do not improve the reaction. Other manipulations to the dibromination reaction are still being examined including the brominating agents hydantoin, N-bromophthalimide, and tribromoisocyanuric acid, along with the base 1,4-diazabicyclo[2.2.2]octane, and adjustments to the reaction temperature and duration. The new dibromination route that this work will produce will provide the scientific community with a novel dibromination pathway and will significantly improve the synthetic route to clavatadine A.

Poster Number

16

Faculty Mentor(s)

Chamberland, Stephen

Additional Mentoring Department

Chemistry

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May 15th, 8:30 AM May 15th, 11:00 AM

The Dibromination of Homogentisic Acid Lactone

SURC Ballroom C/D

The recently described total synthetic pathway to clavatadine A, beneficial for its properties as an anticoagulant, is hindered by a step involving the dibromination of homogentisic acid lactone. This step produces moderate yields and mixed products preventing the discovered pathway from being practical in industrial production. Consequently, the efficiency of the dibromination step will be improved so that it results in at least an 80 percent yield and in a single product. In developing this alternative route many variables have been manipulated including the bromine source, base type, and reaction conditions. This work has revealed that the brominating agent N-bromosuccinimide, the bases pyridine, lithium acetate, potassium acetate, imidazole, and N,N-diisopropylethylamine, along with the solvents acetonitrile and tetrahydrofuran, do not improve the reaction. Other manipulations to the dibromination reaction are still being examined including the brominating agents hydantoin, N-bromophthalimide, and tribromoisocyanuric acid, along with the base 1,4-diazabicyclo[2.2.2]octane, and adjustments to the reaction temperature and duration. The new dibromination route that this work will produce will provide the scientific community with a novel dibromination pathway and will significantly improve the synthetic route to clavatadine A.