仿生单线态氧氧化研究：在生物碱西蒙林碱合成中的应用。

Studies on Biomimetic Singlet Oxygen Oxidations: Application to the Synthesis of the Alkaloid Simulenoline.

机构信息

Instituto de Química Rosario, Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario-CONICET, Suipacha 531, S2002LRK, Rosario, Argentina.

出版信息

J Nat Prod. 2020 Apr 24;83(4):1309-1313. doi: 10.1021/acs.jnatprod.0c00210. Epub 2020 Apr 1.

DOI:10.1021/acs.jnatprod.0c00210

PMID:32233438

Abstract

The synthesis of the biologically active alkaloid simulenoline, isolated from the roots of , is reported. The natural product was assembled from simple commercial reagents via initial domino Knoevenagel/oxa-6π-electrocyclization followed by a one-pot singlet-oxygen ene-reaction/reduction sequence. New insights of singlet oxygen reactivity with olefinic substrates have been revealed.

摘要

报告了从的根部分离出的生物活性生物碱 simulenoline 的合成。该天然产物是通过初始的多步 Knoevenagel/氧杂-6π-电环化反应，然后通过一锅 singlet-oxygen ene-反应/还原序列，由简单的商业试剂组装而成。揭示了单线态氧与烯烃底物反应的新见解。