Stereocontrolled Synthesis of the Aminocyclopentitol Core of Jogyamycin via an Ichikawa Rearrangement Reaction
Year: 2019
Type: article
Abstract: Jogyamycin is a member of the aminocyclopentitol class of natural products that exhibits significant antiprotozoal activities against diseases that include African sleeping sickness and malaria. Herein, we report a route to the core of this natural product via an underutilized Ichikawa rearrangement as a key step. This route efficiently forms the cyclopentane ring from simple and easily accessible starting materials and rapidly installs the C1/C4/C5 polar functional groups. In addition, this strategy shows excellent potential for the preparation of analogues of jogyamycin to study how structural changes impact the selectivity in binding to the ribosome.
Source: The Journal of Organic Chemistry
Authors: Nels C. Gerstner, Jennifer M. Schomaker
Institution: University of Wisconsin–Madison
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: green
Awards: Synthetic approaches to complex amines that inhibit protein synthesis by impacting the ribosome, G1887742554, Enantioselective Synthesis of Jogyamycin and Development of a Predictive Binding Model Enabled by Analog Synthesis, Laser-Enhanced NMR Instrumentation for Chemical and Biochemical Research, NMR SPECTROMETER, G9000304385
OpenAlex ID: W2977576996