%0 Journal Article
%@ 0008-4042
%A Wipf, P
%A Grenon, M
%D 2006
%F pittir:22504
%J Canadian Journal of Chemistry
%N 10
%P 1226 - 1241
%T Toward the total synthesis of lophotoxin - New methodologies and synthetic strategies
%U http://d-scholarship-dev.library.pitt.edu/22504/
%V 84
%X Our recent progress toward the synthesis of the furanocembranolide lophotoxin (1) is disclosed. Strategies for the stereoselective incorporation of the C13 stereocenter by a catalytic desymmetrization of a cyclic meso-anhydride, as well as a novel 1,6-addition reaction of organocuprates to unsaturated [1,3]dioxin-4-ones are discussed. Preliminary results on the development of a rhodium-catalyzed asymmetric 1,6-addition reaction are also mentioned. Finally, modifications of a previously reported transition-metal- catalyzed cyclization reaction involving α-propargyl β-keto esters allow furan ring formation either under thermal conditions or by microwave irradiation. © 2006 NRC.