Total Synthesis of Aetheramide A.
The first total synthesis of the highly potent anti-HIV natural product aetheramide A was accomplished in 18 steps from four equally complex building blocks. The synthesis established the unknown configuration at C26 and used a configurationally labile β-ketoester moiety for the self-adjustment of the configuration at a methyl branch. The pivotal macrolactamization was achieved by trapping a thermally generated acylketene which was derived from its corresponding dioxinone.
Institute for Organic Chemistry, Leibniz Universität Hannover, and, Centre of Biomolecular Drug Research (BMWZ), Schneiderberg 1B, 30167, Hannover, Germany.
Lisa
L
Gerstmann
Institute for Organic Chemistry, Leibniz Universität Hannover, and, Centre of Biomolecular Drug Research (BMWZ), Schneiderberg 1B, 30167, Hannover, Germany. markus.kalesse@oci.uni-hannover.de.|Helmholtz Centre for Infection Research (HZI), Inhoffenstr. 7, 38124, Braunschweig, Germany. markus.kalesse@oci.uni-hannover.de.
Markus
http://orcid.org/0000-0003-4858-3957
M
Kalesse
D000447:Aldehydes / Q000737:chemistry*; D019380:Anti-HIV Agents / Q000138:chemical synthesis* / Q000737:chemistry; D047630:Depsipeptides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure
D000447:Aldehydes; D019380:Anti-HIV Agents; D047630:Depsipeptides; C574677:aetheramide A
aetheramide; anti-HIV; macrocyclization; structure elucidation; vinylogous Mukaiyama aldol reaction