A common approach to the total synthesis of l-arabino-, l-ribo-C18-phytosphingosines, ent-2-epi-jaspine B and 3-epi-jaspine B from d-mannose

Martinková, Miroslava; Pomikalová, Kvetoslava; Gonda, Jozef; Vilková, Mária

doi:10.1016/j.tet.2013.07.028

Cited by 25 publications

(9 citation statements)

References 76 publications

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“…Examples of the total synthesis of important natural compounds will be presented and discussed in a comprehensive way. It should be emphasized that the examples discussed are the authors' selection; other important natural scaffolds also use the Wittig reaction as a key step, for example dienamines, 2 H ‐azirine, sphingolipids, macrolides, and pyrenes, but these were not discussed herein.…”

Section: Total Synthesis Of Natural Heterocyclic Compoundsmentioning

confidence: 99%

Applications of the Wittig Reaction on the Synthesis of Natural and Natural‐Analogue Heterocyclic Compounds

2018

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More than sixty years after its discovery, the Wittig reaction still is a powerful tool to create carbon–carbon double bonds. The large diversity of high‐yielding and stereoselective reactions that can be achieved, even for highly functionalized molecules, is presented, demonstrating that the Wittig reaction is an efficient and attractive strategy in synthetic organic chemistry. The principles of the reaction will be briefly presented and discussed, but the focus will be on the most recent reports using this reaction in the synthesis of heterocyclic compounds. A comprehensive discussion on its application in the total synthesis of natural products and in the synthesis of natural analogues will be presented. Emphasis will be given to important organic molecules that present interesting biological activities. The purpose of this short review is to highlight the advances in this general area by presenting such newer applications in organic synthesis and eventually guide future researchers.

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Section: Total Synthesis Of Natural Heterocyclic Compoundsmentioning

confidence: 99%

Applications of the Wittig Reaction on the Synthesis of Natural and Natural‐Analogue Heterocyclic Compounds

2018

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“…In 2013, Martinková and co-workers described the total synthesis of protected L g -arabino-phytosphingosine 31 and L-ribo-phytosphingosine 28 from 2,3:5,6-di-O-isopropylidene-D-mannofuranose (Scheme 4; g = glyceraldehyde). 19 The pivotal reactions involved [3,3]-sigmatropic rearrangement to introduce the desired amino functionality, and chain elongation through Wittig olefination. Notably, thermal Overman rearrangement of 24 furnished an inseparable mixture of rearranged products in low yield and poor diastereoselectivity, while the use of microwave heating afforded high yields of rearranged products and greatly shortened reaction times.…”

Section: Chirality From Mannose or Mannitolmentioning

confidence: 99%

Recent Progress in Chemical Syntheses of Sphingosines and Phytosphingosines

Gao

Ding

et al. 2016

Synthesis

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Sphingolipids and their derivatives such as glycosphingolipids and sphingomyelins exist ubiquitously in biomembrane of all eukaryotic cells, which play pivotal roles in cell proliferation, recognition, adhesion, and signal transduction. Sphingosine is shown to be the important lipid moiety in the large majority of glycosphingolipids and sphingomyelins, while phytosphingosine is one of the major long-chain moieties of glycosphingolipids. Due to the significance of the two bioactive lipids, tremendous efforts have been made to synthesize sphingosine or phytosphingosine using chiral pool approaches, chiral auxiliary and asymmetric reactions to construct the continuous stereogenic centers in them. This review covers the synthetic literatures published in the year after 2000.

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“…L-serine [ 7 – 18 ], or by asymmetric catalysis [ 19 – 25 ]. Several publications also focused on the synthesis of stereoisomers of the natural product [ 4 , 12 , 16 – 17 19 , 26 – 28 ] because these compounds also showed comparable biological activities [ 4 – 5 ].…”

Section: Introductionmentioning

confidence: 99%

Stereodivergent synthesis of jaspine B and its isomers using a carbohydrate-derived alkoxyallene as C₃-building block

Schmiedel¹,

Stefani²,

Reißig³

2013

Beilstein J. Org. Chem.

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SummaryHerein we present the synthesis of the anhydrophytosphingosine jaspine B and three of its stereoisomers using a carbohydrate-derived alkoxyallene in order to obtain the products in enantiopure form. Key step of the reaction sequence is the addition of the lithiated alkoxyallene to pentadecanal, setting the configuration at the later C-2 of the ring system. This reaction step proceeds with moderate selectivity and therefore leads to a stereodivergent approach to the natural product and its enantiomer. The gold-catalyzed 5-endo-cyclization affords the corresponding dihydrofurans, which after separation, azidation of the enol ether moiety and two subsequent reduction steps give the natural product and its stereoisomers.

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A common approach to the total synthesis of l-arabino-, l-ribo-C18-phytosphingosines, ent-2-epi-jaspine B and 3-epi-jaspine B from d-mannose

Cited by 25 publications

References 76 publications

Applications of the Wittig Reaction on the Synthesis of Natural and Natural‐Analogue Heterocyclic Compounds

Applications of the Wittig Reaction on the Synthesis of Natural and Natural‐Analogue Heterocyclic Compounds

Recent Progress in Chemical Syntheses of Sphingosines and Phytosphingosines

Stereodivergent synthesis of jaspine B and its isomers using a carbohydrate-derived alkoxyallene as C₃-building block

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A common approach to the total synthesis of l-arabino-, l-ribo-C18-phytosphingosines, ent-2-epi-jaspine B and 3-epi-jaspine B from d-mannose

Cited by 25 publications

References 76 publications

Applications of the Wittig Reaction on the Synthesis of Natural and Natural‐Analogue Heterocyclic Compounds

Applications of the Wittig Reaction on the Synthesis of Natural and Natural‐Analogue Heterocyclic Compounds

Recent Progress in Chemical Syntheses of Sphingosines and Phytosphingosines

Stereodivergent synthesis of jaspine B and its isomers using a carbohydrate-derived alkoxyallene as C3-building block

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Stereodivergent synthesis of jaspine B and its isomers using a carbohydrate-derived alkoxyallene as C₃-building block