title: Stereoselective routes to aryl substituted γ-butyrolactones and their application towards the synthesis of highly oxidised furanocembranoids.
abstract: Titanium chelate addition of aryl nucleophiles to cyclopropyl aldehyde 6 followed by a tin-catalyzed one-pot retro-aldol, acetalisation and lactonisation sequence afforded cis and trans γ-aryllactone acetals. A γ-furyllactone derived by this approach was further transformed in two steps to model compounds for the oxidised northeastern sectors of selected Pseudopterogorgia diterpenoids.
authors: Institut für Organische Chemie, Universität Regensburg, Universitätsstrasse 31, Regensburg, D-93053, Germany.
authors: Allan Patrick G
authors: AP
authors: Macabeo
authors: Andreas
authors: A
authors: Kreuzer
authors: Oliver
authors: O
authors: Reiser
mesh_terms: D015107:4-Butyrolactone / Q000737:chemistry*; D004224:Diterpenes / Q000138:chemical synthesis*; D005663:Furans / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013237:Stereoisomerism
chemical_list: D004224:Diterpenes; D005663:Furans; D015107:4-Butyrolactone; C039281:furan