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Total synthesis of lycogarubin C utilizing the Kornfeld–Boger ring contraction

✍ Scribed by Liangfeng Fu; Gordon W. Gribble

Publisher: Elsevier Science
Year: 2010
Tongue: French
Weight: 320 KB
Volume: 51
Category: Article
ISSN: 0040-4039
DOI: 10.1016/j.tetlet.2009.11.085

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✦ Synopsis

An efficient synthesis of lycogarubin C (3) was completed in seven steps from the known 1-(phenylsulfonyl)indole-3-carbaldehyde in 30% overall yield, via a Diels-Alder reaction between (Z)-1,2-di(1H-indol-3-yl)ethene 9b and dimethyl 1,2,4,5-tetrazine-3,6-dicarboxylate (7), followed by a Kornfeld-Boger ring contraction to form the pyrrole ring.

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