Journal article
Stereocontrolled Synthesis of the Aminocyclopentitol Core of Jogyamycin via an Ichikawa Rearrangement Reaction
Journal of organic chemistry, Vol.84(21), pp.14092-14100
11/01/2019
DOI: 10.1021/acs.joc.9b02249
PMCID: PMC6944531
PMID: 31578059
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.
Details
- Title: Subtitle
- Stereocontrolled Synthesis of the Aminocyclopentitol Core of Jogyamycin via an Ichikawa Rearrangement Reaction
- Creators
- Nels C. Gerstner - University of Wisconsin–MadisonJennifer M. Schomaker - University of Wisconsin–Madison
- Resource Type
- Journal article
- Publication Details
- Journal of organic chemistry, Vol.84(21), pp.14092-14100
- DOI
- 10.1021/acs.joc.9b02249
- PMID
- 31578059
- PMCID
- PMC6944531
- NLM abbreviation
- J Org Chem
- ISSN
- 0022-3263
- eISSN
- 1520-6904
- Publisher
- Amer Chemical Soc
- Number of pages
- 9
- Grant note
- 1R01GM111412; F31GM122300-02; RR08389-01 / NIH; United States Department of Health & Human Services; National Institutes of Health (NIH) - USA CHE-9208463; CHE-9629688 / NSF; National Science Foundation (NSF) R01GM111412 / NATIONAL INSTITUTE OF GENERAL MEDICAL SCIENCES; United States Department of Health & Human Services; National Institutes of Health (NIH) - USA; NIH National Institute of General Medical Sciences (NIGMS)
- Language
- English
- Date published
- 11/01/2019
- Academic Unit
- Chemistry
- Record Identifier
- 9984934670502771
Metrics
2 Record Views