A New Strategy for the Reiterative Synthesis of trans-Fused Tetrahydropyrans via Alkylation of Oxiranyl Anion and 6-endo Cyclization

Recent Applications of the Suzuki-Miyaura Cross-coupling to Complex Polycyclic Ether Synthesis

“…Benzylation, ozonolysis of the double bond followed by reductive workup, a second benzylation, and acid hydrolysis of the benzylidene acetal afforded diol 23. Sequential tri ation and TBS protection in a one pot operation according to the Mori procedure, 38 was followed by CuI catalyzed displacement with allylmagnesium bromide to give alkene 24. Wacker Tsuji oxidation 39 using a PdCl 2 /Cu(OAc) 2 system 40 provided methyl ketone 25.…”

Total Synthesis of Structurally Complex Marine Oxacyclic Natural Products

“…A four-step sequence involving benzylation, ozonolysis/reduction, benzylation, and deprotection of the benzylidene acetal gave diol 107. Application of one-pot selective triflation/silylation 64 followed by alkylation of the resultant triflate with allylmagnesium bromide/CuBr 65 yielded olefin 108, which was converted to aldehyde 109 in five steps. Exposure of 109 to SmI 2 in THF/MeOH at room temperature delivered, after acid treatment, lactone 110 as a single stereoisomer.…”

Die Entdeckung und Synthese von marinen Polyethern

“…[64] Schema 18. Die Bildung von Etherringen durch Addition eines Oxiranylanions mit anschließender Cyclisierung (Mori et al, 1996). [65] Schema 19.…”

“…Die Bildung von Etherringen durch Addition eines Oxiranylanions mit anschließender Cyclisierung (Mori et al, 1996). [65] Schema 19. Kreuzkupplungen mit Vinylphosphaten bei der Bildung von Etherringen (a: Nicolaou et al, 1997; [67] b: Sasaki et al, 1999).…”