title: Stereoselective synthesis of (-)-acanthoic acid.
abstract: [reaction: see text] The first stereoselective synthesis of (-)-acanthoic acid (1) has been designed and accomplished. Our synthetic plan departs from (-) Wieland-Miesher ketone (7) and calls upon a Diels-Alder cycloaddition reaction for the construction of the C ring of 1. The described synthesis confirms the proposed stereochemistry of 1 and represents an efficient entry into an unexplored class of biologically active diterpenes.
authors.affiliation: Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, California 92093-0358, USA.
authors.forename: T
authors.initials: T
authors.lastname: Ling
authors.forename: B A
authors.initials: BA
authors.lastname: Kramer
authors.forename: M A
authors.initials: MA
authors.lastname: Palladino
authors.forename: E A
authors.initials: EA
authors.lastname: Theodorakis
mesh_terms: D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000138:chemical synthesis* / Q000737:chemistry; D018360:Crystallography, X-Ray; D003500:Cyclization; D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D007202:Indicators and Reagents; D007723:Korea; D008968:Molecular Conformation; D018517:Plant Roots / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000894:Anti-Inflammatory Agents, Non-Steroidal; D004224:Diterpenes; D007202:Indicators and Reagents; C099958:acanthoic acid