Wipf, P and Grenon, M
(2006)
Toward the total synthesis of lophotoxin - New methodologies and synthetic strategies.
Canadian Journal of Chemistry, 84 (10).
1226 - 1241.
ISSN 0008-4042
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Abstract
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.
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