Model For Total Synthesis of Puraquinonic Acid - CHEM 396 Undergraduate Research Project Application Form

Supervisor's Name: James Gleason

Supervisor's Email: jim.gleason [at] mcgill.ca

Supervisor's Phone: x5596

Supervisor's Website: gleason-group.mcgill.ca

Supervisor's department: Chemistry

Course number: CHEM 396 (Chemistry)

Term: Fall 2014-2015

Project start date: September 2

Project end date: December 4

Project title: Model For Total Synthesis of Puraquinonic Acid

Project description (50-100 words suggested): Puraquinonic acid is an illudalane natural product which possesses mild HL-60 differentiation activity. We have previously reported a 12-step enantioselective synthesis of puraquinonic acid which used our bicyclic thioglycolate lactam alkylation chemistry (Organic Letters, 2006, 8, 1359) to set the key quaternary carbon stereocenter (Angew. Chem. Int. Ed. 2013, 52, 3442). In this project, the quaternary stereocenter was formed at the beginning of the synthesis and carried through the entire synthetic route. This project will examine a new route where the stereocenter is formed at the very end of the synthesis, which should, in theory, be more efficient. The goal of this project will be to study a model alkylation of a 2,3-dibromomethylarene (e.g., 2,3-bis(bromomethyl)-toluene) to see if the generation and alkylation of cyclic enolates can be accomplished using our methodology. If this is successful, the student will have the opportunity to begin the synthesis of the desired dibromoarene to prepare puraquinonic acid itself.

Prerequisite: Minimum 2 terms completed at McGill + CGPA of 3.3 or higher

Grading scheme (The final report must be worth at least 50% of final grade): Laboratory evaluation: 50%; Final report: 50%

Other project information: Preference will be given to Chemistry Honours and Majors students.

Project status: This project is open to applicant.

How students can apply / Next steps: Bring a printed copy of this application form and your advising transcript to me during office hours.

Ethics, safety, and training: Supervisors are responsible for the ethics and safety compliance of undergraduate students. This project involves: Handling chemicals.