title: Asymmetric One-Pot Synthesis of (3R,3aS,6aR)-Hexahydrofuro[2,3-b]furan-3-ol: A Key Component of Current HIV Protease Inhibitors.
abstract: A concise and efficient synthesis of (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol, a key building block for several clinical and experimental HIV protease inhibitors including the highly important drug darunavir, was achieved via a one-pot procedure using furan and Cbz-protected glycol aldehyde as starting materials. A [2+2]-photocycloaddition between both reactants which can be prepared from wood-based starting materials according to the principles of xylochemistry, followed by hydrogenation and lipase-catalyzed kinetic resolution afforded the target compound in high yield and up to 99% ee.
authors.affiliation: Institute of Organic Chemistry, Johannes Gutenberg University , Duesbergweg 10-14, 55128 Mainz, Germany.
authors.forename: Adrian
authors.initials: A
authors.lastname: Sevenich
authors.affiliation: Institute of Organic Chemistry, Johannes Gutenberg University , Duesbergweg 10-14, 55128 Mainz, Germany.
authors.forename: Gong-Qing
authors.initials: GQ
authors.lastname: Liu
authors.affiliation: Department of Chemistry, The University of Alabama , Tuscaloosa, Alabama 35487, United States.
authors.forename: Anthony J
authors.identifier: 0000-0003-4922-2694
authors.initials: AJ
authors.lastname: Arduengo
authors.affiliation: Department of Chemistry, Virginia Commonwealth University , Richmond, Virginia 23284, United States.
authors.forename: B Frank
authors.initials: BF
authors.lastname: Gupton
authors.affiliation: Institute of Organic Chemistry, Johannes Gutenberg University , Duesbergweg 10-14, 55128 Mainz, Germany.
authors.forename: Till
authors.identifier: 0000-0002-3266-4050
authors.initials: T
authors.lastname: Opatz
mesh_terms: D002625:Chemistry, Organic / Q000379:methods*; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D017320:HIV Protease Inhibitors / Q000138:chemical synthesis*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D005663:Furans; D017320:HIV Protease Inhibitors