The Development and Application of Heterocycle Forming Reactions in Natural Product Total Synthesis
Reisman’s research is focused on the chemical synthesis of “natural products,” molecules that are isolated from plants, fungi, bacteria, and other natural sources. Many natural products exhibit interesting biological properties that may prove useful in medicine. One family of natural products that Reisman is working on is known as the ETPs. Members of this family have a reactive sulfur-sulfur bond, which is proposed to confer many of these molecules with anticancer properties. Reisman and her group are interested in synthesizing a particular subgroup of ETPs that, prior to her research, had never previously been prepared in the laboratory. Reisman received the Cottrell Scholar Award (CSA) based on her peer-reviewed proposal that included both research and teaching projects. Her CSA research project involves the development of new reactions that “isomerize” open-chain molecules to ring-containing molecules. In an isomerization reaction, the number of atoms in the starting molecule and product molecule stays the same, but the bonds between the atoms are rearranged. Reisman proposes to use isomerization reactions to prepare the target ETP molecules in fewer steps and in higher yields from commercially available material. Meanwhile, for her Cottrell Scholar education project, she intends to develop a new freshman seminar at Caltech as part of a new curricular initiative at the school. Her proposed course is entitled, “From Penicillin to the Pill: How Small Molecules Have Changed the Modern World.” It will be open to 10-15 students who will meet with Reisman weekly in an informal, discussion-style setting. “The goal of the course is to excite students about chemical research by exposing them to the practical applications of chemistry very early in their college careers,” Reisman said. As an early-career chemist, Reisman’s work has been called “impressive,” and more senior colleagues have said she shows “exceptional promise” as an academic-based scientist. She received her Ph.D. in organic chemistry at Yale University and did postdoctoral work at Harvard before joining the Caltech faculty.