College Honors Program
Synthetic Studies on Diospongin B: A Cross-Cultural Investigation of Natural Products
Date of Creation
5-2022
Document Type
Campus Access Only
Department
Chemistry
First Advisor
Kevin J. Quinn
Abstract
Natural products have been major targets of organic synthesis for decades. The growing library of naturally occurring products generates a wide range of biologically relevant and structurally complex molecules for researchers to synthesize. This library is largely informed by traditional practices; traditional medicine employs native plants in treatment of various diseases, providing organic chemists with potential targets for isolation, analysis, and eventual synthesis. Analysis of the interface between traditional medicine and organic synthesis using case studies of naturally derived therapeutics reveals how cross-cultural interactions yield medical discovery. Diospongin B is a natural product isolated from the rhizomes of Dioscorea spongiosa, a flowering plant in China notable for its utility in traditional medicine. This compound exhibits potent inhibitory activity on bone resorption, accounting for the plant’s historical application in treating rheumatism. Diospongin B serves as an attractive target not only for its reported biological activities but for the distinctive challenge posed by the trans- stereochemical arrangement of substituents on the six- membered tetrahydropyran ring. We have developed a strategy to the synthesis of diospongin B that employs a sequence which controls the relative 2,6-trans stereochemical relationship via a bicyclic intermediate. We anticipate this strategy will facilitate the total synthesis of diospongin B as well as other natural products with similar structures.
Recommended Citation
Kote, Pamela, "Synthetic Studies on Diospongin B: A Cross-Cultural Investigation of Natural Products" (2022). College Honors Program. 96.
https://crossworks.holycross.edu/honors/96