Recent Progress in Chemical Syntheses of Sphingosines and Phytosphingosines

Abstract

Sphingolipids and their derivatives, such as glycosphingolipids and sphingomyelins, are ubiquitous in the biomembrane of eukaryotic cells, and they play pivotal roles in cell proliferation, recognition, adhesion, and signal transduction. Sphingosine is predominantly the important lipid moiety of the glycosphingolipids and sphingomyelins, while phytosphingosine is a major long-chain moiety for glycosphingolipids. Due to the significance of these two bioactive lipids, tremendous efforts have been made to synthesize sphingosine or phytosphingosine, with chiral pool approaches, chiral auxiliaries, and asymmetric reactions used to construct their contiguous stereogenic centers. This review covers the synthetic literature published from 2000–2015.

1 Introduction

2 Chiral Approach

2.1 Chirality from Sugars

2.2 Chirality from Serine and Its Derivatives

2.3 Chirality from d-ribo-Phytosphingosine

2.4 Chirality from d-Tartaric Acid and Its Diester

2.5 Chirality from Other Chiral Precursors

3 Chiral Auxiliaries

3.1 Chiral Sulfur Auxiliaries

3.2 Chiral N-Containing Auxiliaries

4 Asymmetric Reactions

4.1 Sharpless Dihydroxylation Reaction

4.2 Sharpless Epoxidation and Shi’s Epoxidation Reaction

4.3 Asymmetric Aldol Reaction

4.4 Sharpless Kinetic Resolution

4.5 Asymmetric Aminohydroxylation and Amination

5 Conclusions

Key words

sphingosine - phytosphingosine - synthesis - chiral pool - auxiliary - epoxidation

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