Total syntheses of (±)-fawcettimine, (±)-fawcettidine, (±)-lycoflexine, and (±)-lycoposerramine B
Date
2012
Authors
Pan, Guojun, author
Williams, Robert M., advisor
Henry, Charles, committee member
MacNeil, Maechael, committee member
Rovis, Tomislav, committee member
Wood, John L., committee member
Journal Title
Journal ISSN
Volume Title
Abstract
The total syntheses of (±)-fawcettimine, (±)-lycoflexine, (±)-fawcettidine, and (±)-lycoposerramine B have been accomplished through an efficient, unified, and stereocontrolled strategy that required sixteen, sixteen, seventeen, and seventeen steps, respectively, from commercially available materials. The key transformations involve: 1) a Diels-Alder reaction between a 1-siloxy diene and an enone to construct the cis-fused 6,5-carbocycles with one all-carbon quaternary center, and 2) a Fukuyama-Mitsunobu reaction to form the azonine ring. Access to the enantioselective syntheses of these alkaloids can be achieved by kinetic resolution of the earliest intermediate via a Sharpless asymmetric dihydroxylation.
Description
Rights Access
Subject
fawcettimine
total synthesis
lycoposerramine B
lycoflexine
lycopodium
fawcettidine