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Novel synthesis of the 2-azaanthraquinone alkaloid, scorpinone, based on two microwave-assisted pericyclic reactions

✍ Scribed by Tominari Choshi; Teppei Kumemura; Junko Nobuhiro; Satoshi Hibino

Book ID: 104095315
Publisher: Elsevier Science
Year: 2008
Tongue: French
Weight: 126 KB
Volume: 49
Category: Article
ISSN: 0040-4039
DOI: 10.1016/j.tetlet.2008.04.033

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✦ Synopsis

The total synthesis of the 2-azaanthraquinone alkaloid, scorpinone (4), isolated from the mycelium of a Bispora-like tropical fungus, has been completed in nine steps. The two key steps involve a microwave-assisted thermal electrocyclic reaction for the synthesis of an 8-oxygenated isoquinoline skeleton from a 1-aza 6p-hexatriene system, and a regioselective microwave-assisted [4+2] cycloaddition for the construction of a 2-azaanthraquinone framework.

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