4.6 Article

Efficient iron-mediated approach to pyrano[3,2-a]carbazole alkaloids-first total syntheses of O-methylmurrayamine A and 7-methoxymurrayacine, first asymmetric synthesis and assignment of the absolute configuration of (-)-trans-dihydroxygirinimbine

Journal

ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 9, Issue 7, Pages 2057-2061

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c0ob01088j

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Funding

  1. Japan Society for the Promotion of Science (JSPS)

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oxidative cyclisation provides an efficient approach to pyrano[3,2-a]carbazole alkaloids. Thus, improved routes to girinimbine and murrayacine as well as the first total syntheses of O-methylmurrayamine A and 7-methoxymurrayacine are reported. Asymmetric epoxidation of girinimbine led to (-)-trans-dihydroxygirinimbine and the assignment of its absolute configuration.

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