title: Total synthesis and structural revision of laurefurenynes A and B.
abstract: Structural reassignment: A total synthesis of the proposed structure of (-)-laurefurenyne A has been accomplished that relies on organocatalytic aldehyde α-chlorination and a flexible chlorohydrin-based strategy for stereocontrolled access to the bis-tetrahydrofuran core of the natural product. Analysis of incongruities between the (1) H NMR spectra of synthetic and natural material led to a configurational reassignment for the natural product, which was also confirmed by total synthesis.
authors: Department of Chemistry, Simon Fraser University, Burnaby, V5A 1S6, BC (Canada), Fax: (+1) 1-778-782-3765.
authors: Michael T
authors: MT
authors: Holmes
authors: Robert
authors: R
authors: Britton
mesh_terms: D001688:Biological Products / Q000138:chemical synthesis / Q000737:chemistry*; D002384:Catalysis; D002728:Chlorohydrins / Q000737:chemistry; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D054879:Halogenation; D044722:Laurencia / Q000737:chemistry / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D013237:Stereoisomerism
chemical_list: D001688:Biological Products; D002728:Chlorohydrins; D005663:Furans; C587663:laurefurenyne A; C587662:laurefurenyne B; C018674:tetrahydrofuran
keywords: chlorohydrin; laurefurenyne A; laurencia acetogenins; organocatalysis; total synthesis