普拉西菌素A的固相全合成

Solid-Phase Total Synthesis of Plusbacin A.

作者信息

Takashina Kazuki, Katsuyama Akira, Kaguchi Rintaro, Yamamoto Kazuki, Sato Toyotaka, Takahashi Satoshi, Horiuchi Motohiro, Yokota Shin-Ichi, Ichikawa Satoshi

机构信息

Faculty of Pharmaceutical Sciences, Hokkaido University, Kita-12, Nishi-6, Kita-ku, Sapporo 060-0812, Japan.

Center for Research and Education on Drug Discovery, Hokkaido University, Kita-12, Nishi-6, Kita-ku, Sapporo 060-0812, Japan.

出版信息

Org Lett. 2022 Mar 25;24(11):2253-2257. doi: 10.1021/acs.orglett.2c00667. Epub 2022 Mar 16.

DOI:10.1021/acs.orglett.2c00667

PMID:35293208

Abstract

The total synthesis of the depsipeptide natural product plusbacin A () utilizing solid-phase peptide synthesis (SPPS) was disclosed. A 3-hydroxy-proline derivative compatible with Fmoc SPPS was prepared by a diastereoselective Joullié-Ugi three-component reaction (JU-3CR)/hydrolysis sequence. After peptide elongation on the solid support, cleavage of the peptide from the resin, followed by macrolactamization and global deprotection, gave plusbacin A ().

摘要

报道了利用固相肽合成（SPPS）对缩肽天然产物普拉西辛A（）进行的全合成。通过非对映选择性朱利耶-乌吉三组分反应（JU-3CR）/水解序列制备了一种与Fmoc SPPS兼容的3-羟基脯氨酸衍生物。在固相载体上进行肽链延伸后，将肽从树脂上裂解下来，然后进行大环内酰胺化和整体脱保护，得到普拉西辛A（）。