title: Efficient synthesis of (3R,3aS,6aR)- hexahydrofuro[2,3-b]furan-3-ol from glycolaldehyde.
abstract: A one-step diastereoselective (up to 98:2) synthesis of the bis-furan alcohol of Darunavir and other HIV drug candidates has been achieved utilizing the novel cyclization of glycolaldehyde and 2,3-dihydrofuran. The cycloaddition was catalyzed by a variety of catalysts including those formed from tin(II) triflate and common chiral ligands such as BINAP and Evans's box ligands. An efficient and unique enzymatic process enhanced the enantiomeric purity to provide the target in optically pure form.
authors.affiliation: Chemical Development, GlaxoSmithKline, Research Triangle Park, NC 27709, USA.
authors.forename: Will L
authors.initials: WL
authors.lastname: Canoy
authors.forename: Bob E
authors.initials: BE
authors.lastname: Cooley
authors.forename: John A
authors.initials: JA
authors.lastname: Corona
authors.forename: Thomas C
authors.initials: TC
authors.lastname: Lovelace
authors.forename: Alan
authors.initials: A
authors.lastname: Millar
authors.forename: Aimee M
authors.initials: AM
authors.lastname: Weber
authors.forename: Shiping
authors.initials: S
authors.lastname: Xie
authors.forename: Yong
authors.initials: Y
authors.lastname: Zhang
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D019380:Anti-HIV Agents / Q000138:chemical synthesis*; D002384:Catalysis; D003500:Cyclization; D005663:Furans / Q000737:chemistry*; D008024:Ligands; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D019380:Anti-HIV Agents; D005663:Furans; D008024:Ligands; C513052:hexahydrofuro(2,3-b)furan-3-ol