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Total synthesis of pareitropone via radical anion coupling.

ABSTRACT: A concise (9-step) synthesis of the tropoloisoquinoline alkaloid pareitropone has been achieved starting from 2-bromoisovanillin. The key step features oxidative cyclization of a readily available phenolic nitronate for the convenient construction of the fused tropone ring. This work underscores the synthetic utility of intramolecular oxidative coupling reactions of phenolic nitronates.

SUBMITTER: Hong SK 

PROVIDER: S-EPMC2929295 | biostudies-literature | 2010 Sep

REPOSITORIES: biostudies-literature

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Total synthesis of pareitropone via radical anion coupling.

Hong Suk-Koo SK   Kim Hyeonjeong H   Seo Youngran Y   Lee Sang Hyup SH   Cha Jin Kun JK   Kim Young Gyu YG  

Organic letters 20100901 17

A concise (9-step) synthesis of the tropoloisoquinoline alkaloid pareitropone has been achieved starting from 2-bromoisovanillin. The key step features oxidative cyclization of a readily available phenolic nitronate for the convenient construction of the fused tropone ring. This work underscores the synthetic utility of intramolecular oxidative coupling reactions of phenolic nitronates. ...[more]

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