Department of Chemistry and Applied Biosciences, ETH Zürich, Vladimir-Prelog-Weg 4, 8093 Zürich, Switzerland.
Centro de Investigaciones Biológicas Margarita Salas, CSIC, Ramiro de Maetzu 9, 28040 Madrid, Spain.
Org Lett. 2020 Nov 6;22(21):8345-8348. doi: 10.1021/acs.orglett.0c02974. Epub 2020 Oct 12.
We have developed a new method for the stereoselective establishment of the -acyl hemiaminal moiety in zampanolide-type structures that involves the reaction of ()-sorbamide () with BINAL-H and subsequent amide transfer from a putative aluminum carboximidoate complex to the aldehyde moiety of a dactylolide precursor, such as or . The method has enabled the efficient synthesis of 13-desmethylene-(-)-zampanolide (), which was found to be an equipotent cell growth inhibitor as the natural product (-)-zampanolide ().
我们开发了一种新方法，用于在扎潘诺内酯型结构中立体选择性地建立 -酰基半缩醛部分，该方法涉及（）-山梨酰胺（）与 BINAL-H 的反应，以及随后酰胺从假定的铝羧亚胺酯配合物转移到达托内酯前体的醛部分，如或。该方法已能够有效地合成 13-去甲烯基-(-)-扎潘诺内酯（），其被发现作为天然产物 (-)-扎潘诺内酯（）的细胞生长抑制剂等效力。
