title: Total Synthesis and Stereochemical Revision of the Anti-Tuberculosis Peptaibol Trichoderin A.
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.
authors.affiliation: School of Biological Sciences, The University of Auckland , 3A Symonds Street, Auckland 1010, New Zealand.|Maurice Wilkins Centre for Molecular Biodiscovery, The University of Auckland , 3A Symonds Street, Auckland 1010, New Zealand.
authors.forename: Iman
authors.initials: I
authors.lastname: Kavianinia
authors.affiliation: School of Biological Sciences, The University of Auckland , 3A Symonds Street, Auckland 1010, New Zealand.
authors.forename: Lavanya
authors.initials: L
authors.lastname: Kunalingam
authors.affiliation: School of Biological Sciences, The University of Auckland , 3A Symonds Street, Auckland 1010, New Zealand.|Maurice Wilkins Centre for Molecular Biodiscovery, The University of Auckland , 3A Symonds Street, Auckland 1010, New Zealand.
authors.forename: Paul W R
authors.initials: PW
authors.lastname: Harris
authors.affiliation: Maurice Wilkins Centre for Molecular Biodiscovery, The University of Auckland , 3A Symonds Street, Auckland 1010, New Zealand.|Department of Microbiology and Immunology, School of Medical Sciences, University of Otago , 720 Cumberland Street, Dunedin 9054, New Zealand.
authors.forename: Gregory M
authors.initials: GM
authors.lastname: Cook
authors.affiliation: School of Biological Sciences, The University of Auckland , 3A Symonds Street, Auckland 1010, New Zealand.|Maurice Wilkins Centre for Molecular Biodiscovery, The University of Auckland , 3A Symonds Street, Auckland 1010, New Zealand.|School of Chemical Sciences, The University of Auckland , 23 Symonds Street, Auckland 1010, New Zealand.
authors.forename: Margaret A
authors.initials: MA
authors.lastname: Brimble