title: Synthesis of the western half of the lolicines and lolitrems.
abstract: [reaction: see text] The synthesis of the highly substituted indole portion of the complex tremorgenic natural products lolicine A and B is presented. The Diels-Alder reaction of a quinone monoimine enables the synthesis of an appropriately substituted indole. The key step in the synthesis is a tandem isopropenyl cuprate addition/aldol cyclocondensation which provides the necessary functionality for elaboration to the 2,2,5,5-tetramethyltetrahydrofuran.
authors.affiliation: Department of Chemistry, The University of Western Ontario, London, Canada.
authors.forename: Dylan B
authors.initials: DB
authors.lastname: England
authors.forename: Jakob
authors.initials: J
authors.lastname: Magolan
authors.forename: Michael A
authors.initials: MA
authors.lastname: Kerr
mesh_terms: D018360:Crystallography, X-Ray; D003500:Cyclization; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D003904:Mitosporic Fungi / Q000737:chemistry; D008968:Molecular Conformation; D015394:Molecular Structure; D009183:Mycotoxins / Q000138:chemical synthesis* / Q000737:chemistry; D013729:Terpenes / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D007211:Indoles; D009183:Mycotoxins; D013729:Terpenes; C518045:lolicine A; C518046:lolicine B