Stereodivergent Strategy for Neurofuran Synthesis via Palladium-Catalyzed Asymmetric Allylic Cyclization: Total Synthesis of 7-epi-ST-Δ8-10-Neurofuran

被引：20

作者：

Valli, Matteo ^{[1
]}

Bruno, Paolo ^{[1
]}

Sbarbada, Davide ^{[1
]}

Porta, Alessio ^{[1
]}

Vidari, Giovanni ^{[1
]}

Zanoni, Giuseppe ^{[1
]}

机构：

[1] Univ Pavia, Dept Chem, I-1027100 Pavia, Italy

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 78卷 / 11期

关键词：

OPENING-CROSS METATHESIS; STEREOSELECTIVE INTRODUCTION; RING; STEREOCHEMISTRY; ISOPROSTANE; ALKYLATION; FRAGMENT; STRESS; ACID;

D O I：

10.1021/jo4004647

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Neurofurans are formed in vivo in the human brain as a consequence of an increased oxidative stress, and they could be valuable biomarkers of the neuronal oxidative stress. In this paper, an enantioselective stereodivergent approach to two key neurofuran precursors, belonging to the AC and ST classes, has been developed starting from a single achiral precursor, the meso-diol 11. The absolute configuration of the THF cores was secured by a Pd-catalyzed asymmetric allylic alkylation using (S,S)-L1 and (R,R)-L2 ligands, respectively.

引用

页码：5556 / 5567

页数：12