Issue 7, 2011
From the journal:

Organic & Biomolecular Chemistry

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†‡

Konstanze K. Gruner,a   Thomas Hopfmann,a   Kazuhiro Matsumoto,b   Anne Jäger,a   Tsutomu Katsukib  and  Hans-Joachim Knölker*a  

* Corresponding authors

a Department Chemie, Technische Universität Dresden, Bergstrasse 66, Germany
E-mail: hans-joachim.knoelker@tu-dresden.de
Fax: +49 351-463-37030

b Department of Chemistry, Faculty of Science, Graduate School and Institute for Advanced Study, Kyushu University, Hakozaki, Higashi-ku, Japan

Abstract

Iron-mediated 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.

Graphical abstract: 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

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Article information

DOI
https://doi.org/10.1039/C0OB01088J
Article type
Communication
Submitted
25 Nov 2010
Accepted
05 Jan 2011
First published
06 Jan 2011

Org. Biomol. Chem., 2011,9, 2057-2061

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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

K. K. Gruner, T. Hopfmann, K. Matsumoto, A. Jäger, T. Katsuki and H. Knölker, Org. Biomol. Chem., 2011, 9, 2057 DOI: 10.1039/C0OB01088J

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