Studies toward the total synthesis of the angucyclinone antibiotic aquayamycin

ORGN 397

Nathalie Lebrasseur and Stéphane Quideau. Institut Européen de Chimie et Biologie, Université Bordeaux 1, Pessac, France
The [bis(trifluoroacetoxy)]iodobenzene-mediated oxidative activation of 2-alkoxyarenols of type 3 for dearomatizing nucleophilic substitution with silyl enol ethers is a rapid approach to orthoquinol ethers of type 2. These species constitute key advanced intermediates for the construction of the benz[a]anthracène ABCD tetracyclic skeleton of aquayamycin-like angucyclinones presenting two vicinal oxygen atoms at the AB ring angular positions. Preparation of various appropriately oxygenated bicyclic orthoquinol ethers of type 2 and their exploitation in the construction of the ABC tricyclic system (e.g., 1) via an umpolung strategy using a protected cyanohydrin intermediate will be discussed.

 

Physical Organic, Materials, Heterocycles, Aromatics, Metal-Mediated Reactions
8:00 PM-10:00 PM, Tuesday, September 9, 2003 Hilton New York -- Americas Hall 1, Poster

Division of Organic Chemistry
The 226th ACS National Meeting, New York, NY, September 7-11, 2003