Progress toward the Total Synthesis of Jogyamycin Using a Tandem Ichikawa/Winstein Rearrangement
Year: 2023
Type: article
Abstract: Jogyamycin is a densely functionalized aminocyclopentitol that displays potent antiprotozoal activity. Herein, we report a route toward this natural product that utilizes an unprecedented transformation involving a tandem Ichikawa-Winstein rearrangement to install the C-1/C-2 diamine core. Attempts to further functionalize the C-3/C-4 alkene en route to jogyamycin are also discussed.
Source: Organic Letters
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, Upgrade of an 11.74 Tesla NMR Instrument, G1887742554, G2138717289, Enantioselective Synthesis of Jogyamycin and Development of a Predictive Binding Model Enabled by Analog Synthesis, G3815559812, G3994591615, Purchase of a Routine High Field Nuclear Magnetic Resonance Spectrometer, MRI: Acquisition of a modern single-crystal X-ray diffractometer with a high dynamic range detector, QExactive (Orbitrap) mass spectrometer, NMR SPECTROMETER, G9000304385
OpenAlex ID: W4388524730