赤比宾/异赤比宾吡啶鎓盐合成马钱子碱 C 和 D。

Chichibabin/isoChichibabin pyridinium synthesis of ma'edamines C and D.

机构信息

Department of Materials and Life Sciences, Faculty of Science and Technology, Sophia University, 7-1 Kioicho, Chiyoda-ku, Tokyo 102-8554, Japan.

出版信息

Bioorg Med Chem Lett. 2021 Aug 15;46:128165. doi: 10.1016/j.bmcl.2021.128165. Epub 2021 May 30.

DOI:10.1016/j.bmcl.2021.128165

PMID:34077773

Abstract

Ma'edamines C and D were isolated from an Okinawan marine sponge and exhibited a unique tetrasubstituted pyridinium skeleton. The proposed biosynthetic pathway is similar to that of desmosine and isodesmosine, which are elastin-crosslinking amino acids. In this study, first total synthesis of ma'edamines C and D was achieved via Pr(OTf)-promoted Chichibabin/isoChichibabin pyridinium synthesis starting from the corresponding aldehydes and amine.

摘要

马艾达明 C 和马艾达明 D 从冲绳海洋海绵中分离得到，具有独特的四取代吡啶鎓骨架。该化合物的生物合成途径与弹性蛋白交联氨基酸中的去甲异亮氨酸和异亮氨酸相似。在这项研究中，我们首次通过 Pr(OTf)促进的 Chichibabin/isoChichibabin 吡啶鎓合成，从相应的醛和胺出发，实现了马艾达明 C 和马艾达明 D 的全合成。