When:
Friday, August 24, 2018
11:00 AM - 12:00 PM CT
Where: Ryan Hall, 4003, 2190 Campus Drive, Evanston, IL 60208 map it
Audience: Faculty/Staff - Student - Post Docs/Docs - Graduate Students
Contact:
Mykieu Pham
Group: ChemCore
Category: Academic
"Stereoselective Synthesis of Terpenoid Natural Products"
Professor Peter Metz
Faculty of Chemistry and Food Chemistry - Organic Chemistry I
Technical University of Dresden, Germany
Abstract
The bicyclo[5.3.0]decane (hydroazulene) ring system is present in many natural products. A relay metathesis approach commencing with (S)-citronellal provided rapid access to the plant-derived guaianolide osmitopsin (1) and the proposed structure of 4,5-epoxyosmitopsin (2). The diterpene 3b-hydroxy-7b-kemp-8(9)-en-6-one (3) isolated from the soldier defense secretion of higher termites incorporates the hydroazulene moiety as part of the complex tetracyclic kempane framework. Starting from the Wieland-Miescher ketone, the total synthesis of this kempane has been accomplished using a domino metathesis and a sulfa-Michael addition as the key steps.
Hosted by Professor Karl Scheidt.