Synthetic Studies of Fawcettimine, Mycosporulone, and Daphnipaxinin

Seminar series
Organic Colloquium
Tue, May 28 4:30pm
Cram Conference Room – 3440 Mol Sci
Speaker Dr. Jonah J. Chang
University of California, Los Angeles
Department of Chemistry and Biochemistry

Special Organic Seminar

"Synthetic Studies of Fawcettimine, Mycosporulone, and Daphnipaxinin"

Abstract.  Synthetic studies toward the alkaloid fawcettimine, the fungal metabolite mycosporulone and the hexacyclic alkaloid daphnipaxinin will be presented.  The formal total synthesis of fawcettimine will be discussed along with the application of a cyclopropane-1,1-diester annulation reaction.  Salient features of the mycosporulone study include a retro-aldol/aldol reaction and a proposed revision of the original structural assignment.  Lastly, progress towards the total synthesis of daphnipaxinin will be covered.  Key aspects of the synthesis include the development of a reproducible Fleming oxidation/debenzylation procedure as well as a pyrone-enolate cross-coupling study.