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Total Synthesis and Stereochemical Revision of the Anti-Tuberculosis Peptaibol Trichoderin A
Iman Kavianinia1,2, Lavanya Kunalingam1, Paul W R Harris1,2
1School of Biological Sciences, The University of Auckland , 3A Symonds Street, Auckland 1010, New Zealand.
Abstract:
The first total synthesis of the postulated structure of the aminolipopeptide trichoderin A and its epimer are reported. A late-stage solution phase C-terminal coupling was employed to introduce the C-terminal aminoalcohol moiety. This methodology provides a foundation to prepare analogues of trichoderin A to establish a structure-activity relationship. NMR spectroscopic analysis established that the C-6 position of the 2-amino-6-hydroxy-4-methyl-8-oxodecanoic acid (AHMOD) residue in trichoderin A possesses an (R)-configuration as opposed to the originally proposed (S)-configuration.
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