Access to a Welwitindolinone Core Using Sequential Cycloadditions
Authors:
- Barry M. TrostBTBarry M. Trost
- Patrick J. McDougallPMPatrick J. McDougall
- 16 July 2009
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 11 (16) , 3782-3785
Abstract
A concise approach to the core skeleton of the welwitindolinone alkaloids was developed on the basis of sequential cycloaddition reactions. First, a palladium catalyzed enantioselective [6 + 3] trimethylenemethane cycloaddition onto a tropone nucleus was used to generate the requisite bicyclo[4.3.1]decadiene. Subsequent modifications to the cycloadduct allowed for an intramolecular [4 + 2] cycloaddition to generate the oxindole and complete the core of the natural product family.Keywords
This publication has 10 references indexed in Scilit:
- Asymmetric Synthesis of Bicyclo[4.3.1]decadienes and Bicyclo[3.3.2]decadienes via [6 + 3] Trimethylenemethane Cycloaddition with TroponesJournal of the American Chemical Society, 2008
- Palladium-Catalyzed Asymmetric [3+2] Cycloaddition of Trimethylenemethane with IminesJournal of the American Chemical Society, 2007
- Enantioselective Construction of Spirocyclic Oxindolic Cyclopentanes by Palladium-Catalyzed Trimethylenemethane-[3+2]-CycloadditionJournal of the American Chemical Society, 2007
- Palladium-Catalyzed Asymmetric [3 + 2] Trimethylenemethane Cycloaddition ReactionsJournal of the American Chemical Society, 2006
- Rhodium(I)-Catalyzed Nucleophilic Ring-Opening Reactions of Oxabicyclo Adducts Derived from the [4 + 2]-Cycloaddition of 2-Imido-Substituted FuransThe Journal of Organic Chemistry, 2006
- Intramolecular Amidofuran Cycloadditions across an Indole π-Bond: An Efficient Approach to theAspidospermaandStrychnosABCECoreOrganic Letters, 2002
- Application of Furanyl Carbamate Cycloadditions Toward the Synthesis of Hexahydroindolinone AlkaloidsThe Journal of Organic Chemistry, 2001
- Oxidized Welwitindolinones from Terrestrial Fischerella spp.Journal of Natural Products, 1999
- Microtubule effects of welwistatin, a cyanobacterial indolinone that circumvents multiple drug resistance.Molecular Pharmacology, 1996
- Welwitindolinone analogues that reverse P-glycoprotein-mediated multiple drug resistance.Molecular Pharmacology, 1995