Subject to Change

PHA 6935: Structure Determination of Complex Natural Products

InstructorDr. Hendrik Luesch

Department of Medicinal Chemistry

Health Science Center, P5-27

Tel.: 273-7738

Office HoursMonday 4-6 pm

Course Objectives

This course is designed for graduate students in the field of natural products chemistry. The rigorous structure determination of natural products using modern spectroscopic methods will be discussed. The major objective is for students to be able to elucidate the structure of any organic small molecule at the end of the course. This is an applied, problem-based course.

MeetsTwice a week for 1.5 h (3 credits total)

TextReading material and notes distributed in class. No textbook required.

PrerequisitesStudent is expected to have a basic knowledge of the use of MS, NMR, IR and UV.

Tentative Lecture Schedule

DatesTopics

Weeks 1-2:Steps in structure determination (classical vs. modern methods)

Determination of molecular weight and formula: mass spectrometry

Nature of unsaturation and functional groups: UV and IR

Weeks 3-4:Basic 1D and 2D NMR techniques

NMR spectral information: chemical shifts, multiplicities, coupling constants, types of spectra

Weeks 5-12:Determination of partial structures and assemblage of units into a total gross structure, two-dimensional NMR

Weeks 13-14:Methods for determining relative and absolute stereochemistry

Grading

Evaluations are based on Homework (30%), Midterm Exam (30%) and Final Exam (40%).

Homework assignments are problem sets that students have one week to complete, unless instructed otherwise. The Midterm Exam will occur in the classroom between week 9 and 11, depending on progress made in class. The Final Exam has a take-home format and consists of solving the structure of a complex natural product using spectroscopic data. Students are allowed one week to work on the assignment.

Partial credit will be given. Most homework assignments will be discussed in class upon completion. Results from the Midterm and Final Exam can be individually discussed with the Instructor upon appointment or during office hours.

Miscellaneous

Class attendance is required. Students will be actively engaged in discussions to understand the thought processes when determining structures. Students will be tested on the lecture material and their ability to apply their gained knowledge to original problems.

Students requesting classroom accommodation must first register with the Dean of Students Office. The Dean of Students Office will provide documentation to the student who must then provide this documentation to the Instructor when requesting accommodation.

Students are required to complete assignments and take exams with integrity. Academic dishonesty will not be tolerated. If a student commits academic dishonesty, the academic penalty will be a failing grade in the course. The UF policies and procedures on academic dishonesty will be followed.