Org Lett. 2018 Apr 20;20(8):2369-2373. doi: 10.1021/acs.orglett.8b00700. Epub 2018 Mar 27.
The total synthesis of tambromycin (1), a recently isolated tetrapeptide, is reported. This unusual natural product possesses a highly modified tryptophan-derived indole fragment fused to an α-methylserine-derived oxazoline ring, and a unique noncanonical amino acid residue named tambroline (11). A convergent synthesis of tambromycin was achieved by a 13-step route that leveraged recent developments in the field of C-H functionalization to prepare the complex indole fragment, as well as an efficient synthesis of tambroline that featured a diastereoselective amination of homoproline.
本文报道了最近分离得到的四肽 tambromycin（1）的全合成。该独特的天然产物含有一个高度修饰的色氨酸衍生吲哚片段与一个α-甲基丝氨酸衍生的噁唑啉环融合，以及一个名为 tambroline（11）的独特非典型氨基酸残基。通过 13 步反应的汇聚合成方法实现了 tambromycin 的全合成，该方法利用了 C-H 功能化领域的最新进展来制备复杂的吲哚片段，以及高效合成 tambroline 的方法，其特征在于高非对映选择性地对 homoproline 进行胺化。
