title: Isostrychnine synthesis mediated by hypervalent iodine reagent.
abstract: Althought there are several reported synthetic routes to strychnine, one of the most widely recognized alkaloids, we report an unexplored route with an oxidative dearomatizing process mediated by hypervalent iodine as the key step. The new syntheses of isostrychnine and strychnine have been achieved from an readily available phenol in nine and ten steps. In addition to the key step, these syntheses involve an aza Michael-ether-enol tandem transformation, two heck type cyclizations, a reductive isomerization, and a double reductive amination in cascade leading to the alkaloid main core.
authors.affiliation: Département de chimie, Université du Québec à Montréal, Laboratoire de Méthodologie et Synthèse de Produits Naturels, C.P. 8888, Succ. Centre-Ville, Montréal, H3C 3P8, Québec (Canada), Fax: (+1) 514-987-4054.
authors.forename: Guillaume
authors.initials: G
authors.lastname: Jacquemot
authors.forename: Gaëtan
authors.initials: G
authors.lastname: Maertens
authors.forename: Sylvain
authors.initials: S
authors.lastname: Canesi
mesh_terms: D003500:Cyclization; D007202:Indicators and Reagents / Q000737:chemistry; D007455:Iodine / Q000737:chemistry*; D007536:Isomerism; D010084:Oxidation-Reduction; D019800:Phenol / Q000138:chemical synthesis / Q000737:chemistry; D013331:Strychnine / Q000138:chemical synthesis* / Q000737:chemistry; D031461:Strychnos nux-vomica / Q000737:chemistry
chemical_list: D007202:Indicators and Reagents; D019800:Phenol; D007455:Iodine; D013331:Strychnine
keywords: aromatic ring umpolung; hypervalent iodine; natural products; oxidation; total synthesis