d-红鞘氨醇及其兄弟化合物的合成

Q2 Chemistry

Tetrahedron, asymmetry Pub Date : 2017-09-15 DOI:10.1016/j.tetasy.2017.08.006

Amrita Ghosh, Shital K. Chattopadhyay

引用次数: 4

摘要

以加纳醛衍生的α，β-不饱和酮为关键步骤，建立了一种高效的基于构建块的合成方案，用于合成具有不同链长的3-酮鞘类化合物。由此获得的仿生前体的立体选择性还原提供了d-红鞘氨醇和截断的类似物，总体产量很高。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

A diversity oriented synthesis of d-erythro-sphingosine and siblings

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A diversity oriented synthesis of d-erythro-sphingosine and siblings

An efficient building block-based synthetic protocol has been developed for the synthesis of 3-ketosphingoids with various chain lengths using cross metathesis of a Garner’s aldehyde-derived α,β-unsaturated ketone as the key step. Stereoselective reduction of the biomimetic precursors thus obtained provided d-erythro-sphingosine and truncated anaogues in good overall yields.

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来源期刊

Tetrahedron, asymmetry 化学-无机化学与核化学

CiteScore

4.70

自引率

0.00%

发文量

审稿时长

1 months

期刊介绍： Cessation. Tetrahedron: Asymmetry presents experimental or theoretical research results of outstanding significance and timeliness on asymmetry in organic, inorganic, organometallic and physical chemistry, as well as its application to related disciplines, especially bio-organic chemistry. The journal publishes critical reviews, original research articles and preliminary communications dealing with all aspects of the chemical, physical and theoretical properties of non-racemic organic and inorganic materials and processes. Topics relevant to the journal include: the physico-chemical and biological properties of enantiomers; strategies and methodologies of asymmetric synthesis; resolution; chirality recognition and enhancement; analytical techniques for assessing enantiomeric purity and the unambiguous determination of absolute configuration; and molecular graphics and modelling methods for interpreting and predicting asymmetric phenomena. Papers describing the synthesis or properties of non-racemic molecules will be required to include a separate statement in the form of a Stereochemistry Abstract, for publication in the same issue, of the criteria used for the assignment of configuration and enantiomeric purity.