ORGN 245 |
Nitrogen-tethered orthoquinol acetates as valuable synthons for the synthesis of oxygenated alkaloids
| Laurent Pouységu and Stéphane Quideau. Institut Européen de Chimie et Biologie, Université Bordeaux 1, Pessac, France |
Iodine(III)-mediated oxidative acetoxylation of nitrogen-tethered 2-methoxyphenols, followed by a fluoride- or base-induced regioselective intramolecular nucleophilic addition reaction, is a two-step sequence of interest for the preparation of functionalized indole and quinoline derivatives. Exploitation of the electrophilicity and differentially activated double bonds of the key intermediates of this heterocyclization methodology, i.e., orthoquinol acetates 1, can be exemplified with the synthesis of oxygenated phenanthridine alkaloid motifs such as 2. Progress toward the use of bis(orthoquinol acetate) synthons in ionic domino reaction aimed at the regiochemically-controlled construction of the ABCD tetracyclic skeleton of the biologically active Amaryllidaceae lycorine (3)-type alkaloids will be also discussed. |
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