title: Formal Synthesis of (+)-Laurencin by Gold(I)-Catalyzed Intramolecular Dehydrative Alkoxylation.
abstract: 8-Membered cyclic ethers are found in a wide range of natural products; however, they are challenging synthetic targets due to enthalpic and entropic barriers. The gold(I)-catalyzed intramolecular dehydrative alkoxylation of ω-hydroxy allylic alcohols was explored to stereoselectively construct α,α'-cis-oxocenes and further applied in a formal synthesis of (+)-laurencin. The gold(I)-catalyzed intramolecular dehydrative alkoxylation may constitute an alternative method for the synthesis of molecular building blocks and natural products that contain highly functionalized 8-membered cyclic ethers.
authors.affiliation: Department of Chemistry, Duke University, Durham, North Carolina, 27708, USA.|Hammond High Magnet School, 45168 River Rd, Hammond, Louisiana, 70401, USA.
authors.forename: Megan L
authors.initials: ML
authors.lastname: Lanier
authors.affiliation: Department of Chemistry, Duke University, Durham, North Carolina, 27708, USA.
authors.forename: Hyeri
authors.initials: H
authors.lastname: Park
authors.affiliation: Department of Chemistry, Duke University, Durham, North Carolina, 27708, USA.
authors.forename: Paramita
authors.initials: P
authors.lastname: Mukherjee
authors.affiliation: Department of Chemistry, Duke University, Durham, North Carolina, 27708, USA.
authors.forename: Jacob C
authors.initials: JC
authors.lastname: Timmerman
authors.affiliation: Duke University NMR Center and Department of Radiology, Duke University, Durham, North Carolina, 27710, USA.
authors.forename: Anthony A
authors.initials: AA
authors.lastname: Ribeiro
authors.affiliation: Department of Chemistry, Duke University, Durham, North Carolina, 27708, USA.
authors.forename: Ross A
authors.initials: RA
authors.lastname: Widenhoefer
authors.affiliation: Department of Chemistry, Duke University, Durham, North Carolina, 27708, USA.
authors.forename: Jiyong
authors.identifier: http://orcid.org/0000-0002-5253-0949
authors.initials: J
authors.lastname: Hong
mesh_terms: D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D004988:Ethers, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry; D006046:Gold / Q000737:chemistry*; D035964:Oxocins / Q000138:chemical synthesis* / Q000737:chemistry; D020005:Propanols / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D001688:Biological Products; D004988:Ethers, Cyclic; D035964:Oxocins; D020005:Propanols; C017460:laurencin; C006463:allyl alcohol; D006046:Gold
keywords: (+)-laurencin; dehydrative alkoxylation; gold catalysis; natural products; ω-hydroxy allylic alcohols