title: Two concise enantioselective total syntheses of (-)-glabrescol implicate alternative biosynthetic pathways starting from squalene.
abstract: The C(2)-symmetric (-)-glabrescol was synthesized in two steps from (10S,11R)-dihydroxy-10,11-dihydrosqualene or squalene with 50% or 10% overall yields, respectively. These highly efficient and biomimetic syntheses employed a base-promoted middle-to-terminal double epoxide-opening cascade, which constructs the five tetrahydrofuran rings in glabrescol in one operation.
authors: State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin, 300071, China.
authors: Peng
authors: P
authors: Yang
authors: Pei-Fang
authors: PF
authors: Li
authors: Jin
authors: J
authors: Qu
authors: Liang-Fu
authors: LF
authors: Tang
mesh_terms: D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013185:Squalene / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D005663:Furans; C116803:glabrescol; D013185:Squalene