The goal of the proposed research is to define the first synthetic route toward 6-hydroxypunctaporonin E, a polycyclic natural product. 6-Hydroxypunctaporonin E was isolated from the fungicolous fungi Pestalotiopsis disseminata, collected in the state of Georgia, and was shown to have antibiotic properties inhibiting the growth of Bacillus subtilis and Staphylococcus aureas.[1] The proposed synthetic route includes an unusual example of the Diels-Alder reaction between a vinylcyclobutene and a dihydrofuranone. Included with the synthetic goal are the design of a novel chiral Lewis acid for Diels-Alder chemistry, and the study of a 6-hydroxypunctaporon E conjugate.

Public Health Relevance

The development of broadly applicable antibiotic medicines is one of mankind's noteworthy accomplishments of the last century. Unfortunately, bacteria have begun to develop resistance to common medications used in the treatment of bacterial infections. As a result there is a continued need for research into the synthesis and biological evaluation of new compounds with antibiotic properties, to better understand their potential as new antibiotics of the future.

Agency
National Institute of Health (NIH)
Institute
National Institute of General Medical Sciences (NIGMS)
Type
Postdoctoral Individual National Research Service Award (F32)
Project #
5F32GM090547-02
Application #
8179901
Study Section
Special Emphasis Panel (ZRG1-F04A-B (20))
Program Officer
Gerratana, Barbara
Project Start
2010-07-19
Project End
2012-07-18
Budget Start
2011-07-19
Budget End
2012-07-18
Support Year
2
Fiscal Year
2011
Total Cost
$40,548
Indirect Cost
Name
Swiss Federal Institute of Tech (Eth Zurich)
Department
Type
DUNS #
481907673
City
Zurich
State
Country
Switzerland
Zip Code
8092
McLaughlin, Martin; Yazaki, Ryo; Fessard, Thomas C et al. (2014) Oxetanyl peptides: novel peptidomimetic modules for medicinal chemistry. Org Lett 16:4070-3