Toward the total synthesis of lophotoxin — New methodologies and synthetic strategies
2006; NRC Research Press; Volume: 84; Issue: 10 Linguagem: Inglês
10.1139/v06-073
ISSN1480-3291
Autores Tópico(s)Synthetic Organic Chemistry Methods
ResumoOur recent progress toward the synthesis of the furanocembranolide lophotoxin (1) is disclosed. Strategies for the stereoselective incorporation of the C 13 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.Key words: 1,6-addition, organocuprates, catalytic desymmetrization, furan cyclization, microwave.
Referência(s)