title: Synthesis and determination of the absolute configuration of cavicularin by a symmetrization/asymmetrization approach.
abstract: Taking the strain: The asymmetric total synthesis and stereochemical assignment of (-)-cavicularin, which features a highly strained polycyclophane ring system, has been achieved. The key features of this synthesis are 1) macrocyclization by an SN Ar reaction, 2) group-selective reaction to induce planar chirality in a highly stereoselective manner, and 3) radical transannulation to construct the highly strained ring system.
authors: Department of Chemistry, Tokyo Institute of Technology, 2-12-1, O-okayama, Meguro-ku, Tokyo, 152-8551 (Japan).
authors: Hiromu
authors: H
authors: Takiguchi
authors: Ken
authors: K
authors: Ohmori
authors: Keisuke
authors: K
authors: Suzuki
mesh_terms: D018360:Crystallography, X-Ray; D003500:Cyclization; D004988:Ethers, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry*; D008968:Molecular Conformation; D013237:Stereoisomerism; D000097566:Cyclophanes
chemical_list: D004988:Ethers, Cyclic; C513696:cavicularin; D000097566:Cyclophanes
keywords: asymmetric synthesis; atropisomerism; cavicularin; cyclophanes; natural products