Institute of Chemistry
Topic
Enantioselective synthesis of hawaiienol A and its analogues
PhD. program
Organic chemistry
Name of the supervisor
Ing. Maroš Bella, PhD.
Contact:
Receiving school
Faculty of Chemical and Food Technology, Slovak University of Technology
Annotation
Hawiienol A is a polyoxygenated p-terphenyl possessing the first naturally occurring 4,7-dioxatricyclo[3.2.1.03,6]octane skeleton. It was isolated from the fungus Paraconiothyrium hawaiiense in 2018 and exhibits a strong cytotoxic activity, comparable with cisplatin. Our proposed 8-step synthesis of the natural product is based on two key reactions: 1. enantioselective Diels-Alder reaction leading to the oxanorbornane motif; 2. intramolecular epoxide opening generating the oxetane ring. Employing structurally diverse furans and dienophiles in the DA reaction should allow for a rapid synthesis of hawaiienol analogues and hence determination of the pharmacophore.