Synthesis of the C42–C52 part of ciguatoxin CTX3C

Phenyl 4,6-di-O-acetyl-2,3-dideoxy-1-thio-α-D-erythro-hex-2-enopyranoside

“…For the synthesis of pseudoglycals utilizing the Ferrier arrangement, see: Ló pez et al (1995); Yadav et al (2001). For applications of pseudoglycals, see: Domon et al (2005); Danishefsky & Bilodeau (1996); Griffith & Danishefsky (1991); Halcomb et al (1995); Bracherro et al (1998); Dorgan & Jackson (1996); Chambers et al (2005); Minuth & Boysen (2009). For background to the synthetic methodology of glycosides, see: Kinfe et al (2011).…”

“…Since the reaction proceeds via an oxycarbonium intermediate, thiols, halides and other nucleophiles can be employed besides alcohols to produce corresponding glycosides (see López et al, 1995;Yadav et al, 2001). The pseudoglycal products from the Ferrier rearrangement reaction have been used as chiral building blocks in the synthesis of antibiotics (see Domon et al, 2005), oligosaccharides (see Danishefsky & Bilodeau, 1996;Griffith & Danishefsky, 1991;Halcomb et al, 1995), nucleosides (see Bracherro et al, 1998), glycopeptides (see Dorgan & Jackson, 1996;Chambers et al, 2005) and also as chiral ligands in asymmetric synthesis (see Minuth & Boysen, 2009).…”

Nitroxide‐Catalyzed Alcohol Oxidations in Organic Synthesis

“…The examples given in Schemes 12.19 and 12.20 again demonstrate the wide functional group tolerance of this method. 99,100 The organic secondary oxidants used here vary from the traditionally used bleach, and are discussed in Section 12.9.…”

The Role Ionic Liquid [BMIM][PF6] in One-Pot Synthesis of Tetrahydropyran Rings through Tandem Barbier–Prins Reaction

“…As reactions of hetero-Diels–Alder [10], iodolactonization reaction [11], selenium etherification of unsaturated alcohols [12], 6-endo cyclization of vinyl epoxides [13], reductive etherification [14], ring closing metathesis [15], Takeda olefination [16], SmI 2 -mediated radical cyclization [17], Iterative epoxide opening cyclization [18], and Prins cyclization reaction are some synthesis methodologies developed aiming at the formation of tetrahydropyran rings.…”