title: Enantiospecific formal total synthesis of the tumor and GSK-3 beta inhibiting alkaloid, (-)-agelastatin A.
abstract: [reaction: see text] An enantiospecific total synthesis of Weinreb's advanced intermediate 2 for (-)-agelastatin A has been achieved from the Hough-Richardson aziridine 8. Noteworthy reactions in our sequence include the highly regioselective trans-diaxial ring-opening of 8 with azide ion to set up the vicinal diamido functionality present within (-)-2 and the Grubbs-Hoveyda ring-closing metathesis (RCM) reaction that was used to construct its cyclopentene core.
authors.affiliation: The Christopher Ingold Laboratories, University College London, 20 Gordon Street, London WC1H 0AJ, England. k.j.hale@ucl.ac.uk
authors.forename: Karl J
authors.initials: KJ
authors.lastname: Hale
authors.forename: Mathias M
authors.initials: MM
authors.lastname: Domostoj
authors.forename: Derek A
authors.initials: DA
authors.lastname: Tocher
authors.forename: Ed
authors.initials: E
authors.lastname: Irving
authors.forename: Feodor
authors.initials: F
authors.lastname: Scheinmann
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D038362:Glycogen Synthase Kinase 3 / Q000037:antagonists & inhibitors*; D000071679:Glycogen Synthase Kinase 3 beta; D023303:Oxazolidinones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D000970:Antineoplastic Agents; D004791:Enzyme Inhibitors; D023303:Oxazolidinones; C464968:agelastatin A; D000071679:Glycogen Synthase Kinase 3 beta; D038362:Glycogen Synthase Kinase 3