Enantioselective Total Synthesis of (+)-Alterbrassicicene C
Noah J. Sims, Weston C. Bonnet, Danielle M. Lawson, John L. Wood
Abstract
Herein, the first total synthesis of (+)-alterbrassicicene C (2) is described. Key features of the synthesis include an oxiranium mediated ether ring expansion, an oxa-Michael/retro-oxa-Michael cascade, and installation of a vinyl methoxy ether moiety via Stille coupling.
Topics & Concepts
ChemistryStille reactionEnantioselective synthesisTotal synthesisMoietyEtherCascadeRing (chemistry)StereochemistryMichael reactionCombinatorial chemistryOrganic chemistryCatalysisChromatography14-3-3 protein interactionsSynthetic Organic Chemistry MethodsSynthesis and Biological Activity