Synthesis of the Leu–Trp Component of the Celogentin Family of Cyclic Peptides Through a C–H Activation–Cross-Coupling Strategy

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Contents Vol 63(3)

doi:10.1071/CH10033

Synthesis of the Leu–Trp Component of the Celogentin Family of Cyclic Peptides Through a C–H Activation–Cross-Coupling Strategy

Barbara T. Y. Li ^A, Jonathan M. White ^A, Craig A. Hutton ^A ^B

^A School of Chemistry and Bio21 Molecular Science and Biotechnology Institute, University of Melbourne, Vic. 3010, Australia.
^B Corresponding author. Email: chutton@unimelb.edu.au





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Australian Journal of Chemistry 63(3) 438–444 http://dx.doi.org/10.1071/CH10033
Submitted: 19 January 2010 Accepted: 25 February 2010 Published online: 26 March 2010

Abstract

A bioinspired approach to the central leucine(C3)–tryptophan(C6) cross-linked moiety present in the celogentin family of cyclic peptide natural products was achieved. The key transformation was enabled through a palladium-catalyzed C–H activation–cross-coupling of leucine quinoline amide and 6-iodotryptophan derivatives. X-Ray crystallographic analysis of a β-(indol-6-yl)-leucine derivative confirms the stereochemistry of the cross-linked adduct matches that of the natural products. The method enables the preparation of the Leu–Trp adduct as a single stereoisomer from l-leucine and l-tryptophan.