基于合成策略的海洋多环醚天然产物的立体化学结构确定。

Synthesis-Driven Stereochemical Assignment of Marine Polycyclic Ether Natural Products.

机构信息

Department of Applied Chemistry, Faculty of Science and Engineering, Chuo University, 1-13-27 Kasuga, Bunkyo-ku, Tokyo 112-8551, Japan.

出版信息

Mar Drugs. 2021 Apr 29;19(5):257. doi: 10.3390/md19050257.

DOI:10.3390/md19050257

PMID:33947080

原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC8145320/

Abstract

Marine polycyclic ether natural products have gained significant interest from the chemical community due to their impressively huge molecular architecture and diverse biological functions. The structure assignment of this class of extraordinarily complex natural products has mainly relied on NMR spectroscopic analysis. However, NMR spectroscopic analysis has its own limitations, including configurational assignment of stereogenic centers within conformationally flexible systems. Chemical shift deviation analysis of synthetic model compounds is a reliable means to assign the relative configuration of "difficult" stereogenic centers. The complete configurational assignment must be ultimately established through total synthesis. The aim of this review is to summarize the indispensable role of organic synthesis in stereochemical assignment of marine polycyclic ethers.

摘要

海洋多环醚天然产物因其令人印象深刻的巨大分子结构和多样化的生物功能而引起了化学界的极大兴趣。这类极其复杂的天然产物的结构分配主要依赖于 NMR 光谱分析。然而，NMR 光谱分析有其自身的局限性，包括构象灵活系统中手性中心的构型分配。合成模型化合物的化学位移偏差分析是分配“困难”手性中心相对构型的可靠方法。完整的构型分配必须通过全合成最终建立。本文综述的目的是总结有机合成在海洋多环醚立体化学分配中的不可或缺的作用。