This project addresses the development of new synthetic methodology for the formation of five-membered rings, culminating in the synthesis of two five-membered ring containing natural products: the lipoxygenase inhibitor tetrapetalone A and the antibiotic diterpenoid guanacastepene A, which has shown activity against vancomycin resistant staphylococci. In addition to applications in natural product synthesis, these new transformations may offer insight into reactivity such as the importance of allylic strain and anchimeric effects in accelerating pericyclic processes. For example, investigations of applications to the natural product tetrapetalone A have revealed a substituent accelerating effect in a dienyl aryl ketone Nazarov reaction. Additionally, a unique connection has been made between pyrans and alpha-acyloxy cyclopentenones that may find broad application in complex molecule synthesis. The PI will be actively involved in serving as a mentor and facilitator for minority and women interested in pursuing careers in the sciences. He will serve as a sponsor for three minority undergraduates in the UC LEADS program at UC Berkeley, as a mentor for the minority MAP program at Jackson State University, and as a facilitator with chemistry outreach programs at Oakland High School and Northern Light Middle School in Oakland. Each of these programs serves a large number of minority and financially disadvantaged students.
With the support of this CAREER award from the Organic and Macromolecular Chemistry Program, Professor Richmond Sarpong, of the Department of Chemistry at the University of California at Berkeley, is developing new reactions applicable to the controlled and efficient synthesis of complex organic molecules. Five-membered rings occur in a wide variety of natural products that possess important biological activity. Although a number of strategies have been developed for the synthesis of five-membered rings, there remains a need for synthetic transformations that provide these types of compounds with the necessary "handles" for conversion into more complex products. Professor Sarpong is also actively involved in a variety of programs designed to train a diverse group of scientists, with each of these programs specifically targeting a large number of minority and financially disadvantaged students. He will serve as a sponsor for three minority undergraduates in the UC LEADS program at UC Berkeley, as a mentor for the minority MAP program at Jackson State University, and as a facilitator with chemistry outreach programs at Oakland High School and Northern Light Middle School in Oakland.
