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有机催化抗坏血酸对α,β-不饱和醛的 1,4-共轭加成:生物启发的白屈菜红碱、白屈菜赤碱和二拉西罗内酯的提议结构的全合成。

Organocatalytic 1,4-conjugate addition of ascorbic acid to α,β-unsaturated aldehydes: bio-inspired total syntheses of leucodrin, leudrin and proposed structure of dilaspirolactone.

机构信息

The Comprehensive AIDS Research Center, Department of Pharmacology and Pharmaceutical Sciences, School of Medicine, Tsinghua University, Beijing 100084, China.

出版信息

Org Biomol Chem. 2013 Apr 7;11(13):2093-7. doi: 10.1039/c3ob00046j.

DOI:10.1039/c3ob00046j
PMID:23440072
Abstract

The organocatalytic additions of ascorbic acid to various α,β-unsaturated aldehydes via tandem 1,4-conjugate addition/hemiacetalization/hemiketalization were developed, which provided a rapid entry into the 5-5-5 spirodilactone cores of a family of ascorbylated natural products. Based on the described chemistry, total syntheses of leucodrin, leudrin and the proposed structure of dilaspirolactone were achieved.

摘要

通过串联 1,4-共轭加成/半缩醛化/半缩酮化,开发了抗坏血酸对各种α,β-不饱和醛的有机催化加成反应,为一系列抗坏血酸天然产物的 5-5-5 螺二内酯核心提供了快速入口。基于所描述的化学,实现了亮氨酸、左旋糖和拟螺二内酯的全合成。

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