Synthesis 2011(2): 330-336  
DOI: 10.1055/s-0030-1258340
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Total Synthesis of the Slime Mold Alkaloids Arcyroxocin A and B

Guido Mayer, Gregor Wille, Michael Brenner, Kirsten Zeitler, Wolfgang Steglich*
Department Chemie und Biochemie, Ludwig-Maximilians-Universität München, Butenandtstr. 5-13, 81377 München, Germany
Fax: +49(89)218077756 ; e-Mail: wos@cup.uni-muenchen.de ;
Further Information

Publication History

Received 7 October 2010
Publication Date:
08 December 2010 (eFirst)

Abstract

The synthesis of the slime mold pigments arcyroxocin A and B is described. The key step in the synthesis is the oxidative ring closure of an N-protected 3-(4-hydroxyindol-3-yl)-4-indol-3-ylmaleimide with DDQ/PPTS, which affords exclusively the desired arcyroxocin derivative. Attempts to obtain the arcyroxocin system from a 3-(4-hydroxyindolyl)-4-(2-oxoindolinyl)maleimide precursor were less successful and led to oxidative formation of a spiroindoline compound.

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    The claim that arcyroxocin B (4b) was not characterized is unjustified: the UV, ¹H, and ¹³C NMR data of 4b are given in ref. 2a, pp 218 and 223-226.

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1

Responsible for X-ray crystal structure determinations.

10

The exchange of EtMgCl for LiHMDS did not improve the yield (compare, however, ref. 9a).

18

Crystallographic data for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publications no. CCDC 267603 (9a), CCDC 783129 (9b), and CCDC 228174 (20). Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1 EZ, UK [fax: +44 (1223)336033 or e-mail: deposit@ccdc.cam.ac.uk].