Synthesis of the Azaphilones Using Copper-Mediated Enantioselective Oxidative Dearomatization
Authors:
- 10 June 2005
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 127 (26) , 9342-9343
Abstract
An approach to the asymmetric synthesis of the azaphilone natural products is reported involving copper-mediated enantioselective oxidative dearomatization of o-alkynylbenzaldehydes. The approach was successfully applied to the synthesis of (−)-S-15183a and several unnatural azaphilones.Keywords
This publication has 25 references indexed in Scilit:
- Oxidant types in copper–dioxygen chemistry: the ligand coordination defines the Cu n -O2 structure and subsequent reactivityJBIC Journal of Biological Inorganic Chemistry, 2004
- Synthesis of Azaphilones and Related Molecules by Employing Cycloisomerization of o‐AlkynylbenzaldehydesAngewandte Chemie International Edition, 2004
- Reactivity of Dioxygen−Copper SystemsChemical Reviews, 2004
- Complexity with simplicity: a steric continuum of chelating diamines with copper(i) and dioxygenDalton Transactions, 2003
- A Stabilized μ-η2:η2 Peroxodicopper(II) Complex with a Secondary Diamine Ligand and Its Tyrosinase-like ReactivityJournal of the American Chemical Society, 2002
- Synthesis of 7‐acetyloxy‐3,7‐dimethy1‐7,8‐dihydro‐6H‐isochromene‐6,8‐dione and its analoguesJournal of Heterocyclic Chemistry, 2001
- Synthesis of New Chiral 2,2‘-Bipyridyl-Type Ligands, Their Coordination to Molybdenum(0), Copper(II), and Palladium(II), and Application in Asymmetric Allylic Substitution, Allylic Oxidation, and CyclopropanationOrganometallics, 2001
- Asymmetric dihydroxylation of olefins with a simple chiral ligandThe Journal of Organic Chemistry, 1993
- Evidence for a mono-oxygenase mechanism in the biosynthesis of austdiolJournal of the Chemical Society, Chemical Communications, 1983
- Constitution and absolute configuration of austdiol, the main toxic metabolite from Aspergillus ustusJournal of the Chemical Society, Perkin Transactions 1, 1974