38. Review: Synthesis of Cortisone

Freshman Organic Chemistry II (CHEM 125B)

Discoverers of the structure and biological activity of steroid hormones won seven Nobel Prizes between 1927 and 1975. Studying the steps involved in Woodward's 1951 "total" synthesis of cortisone provides a review of the organic reactions covered this semester. Many steps involved novel insights, others were based on lore from previous work In the area. The overall yield of such sequential syntheses is typically much lower than that of convergent syntheses. Practical syntheses of cortisone were based on modification of related steroids readily available from nature. Milestones in total synthesis include both purely intellectual work with natural products and commercially important synthesis of designed pharmaceuticals. The course ends with thanks to those, young and old, who have taught us all.

00:00 - Chapter 1. Steroids and the Medicinal Activity of Cortisone
07:43 - Chapter 2. Woodward's Total Synthesis of Cortisone
33:27 - Chapter 3. Practical Synthesis of Cortisone
38:59 - Chapter 4. Some Milestones in Organic Synthesis
44:59 - Chapter 5. Thanks to Teachers, Colleagues, Family, and Students

Complete course materials are available at the Open Yale Courses website: http://oyc.yale.edu

This course was recorded in Spring 2011.