Synthesis and Biological Evaluation of 1‐Deoxy‐5‐hydroxysphingosine Derivatives

Esteve, Judit; Lorente, Adriana; Romea, Pedro; Urpı́, Fèlix; Rios‐Luci, Carla; Padrón, José M.

doi:10.1002/ejoc.201001268

Cited by 9 publications

(4 citation statements)

References 41 publications

(17 reference statements)

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“…15 Related phytoceramides, obtained upon N-acylation, were described to be more cytotoxic than the corresponding sphingosine-derived ceramides. 16 Other important biologically active phytosphingosine-related compounds have also been reported, 17 including cyclised analogues. 18 In the course of our recent work on the preparation of aza-analogues of the anhydrophytosphingosine jaspine B, we developed a straightforward access to enantioenriched long-chain sphingosine-related epoxyamines (Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

Asymmetric synthesis and cytotoxic activity of isomeric phytosphingosine derivatives

Rives¹,

Baudoin-Dehoux²,

Saffon³

et al. 2011

Org. Biomol. Chem.

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New phytosphingosine analogues have been conceived, synthesised and their cytotoxicity in B16 murine melanoma cells tested. These compounds embed an isomeric substitution pattern resulting from a formal permutation of the C-2 and C-4 substituents along the aliphatic skeleton of the original sphingoid base. Five different stereoisomers have been accessed through regio- and stereocontrolled opening of the oxirane of long chain epoxyamine precursors. The corresponding N-hexyl and N-octanoyl derivatives have also been prepared. In cell viability experiments all the primary amines were found to be more active than the natural phytosphingosine with IC(50) in the low μM range for the most potent compounds.

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Section: Introductionmentioning

confidence: 99%

Asymmetric synthesis and cytotoxic activity of isomeric phytosphingosine derivatives

Rives¹,

Baudoin-Dehoux²,

Saffon³

et al. 2011

Org. Biomol. Chem.

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“…50 The remarkable stereocontrol of the aldol reactions from bromo ketone 88b and the apparent ease of displacing the bromine in S N 2-like processes made the resultant aldols suitable substrates for their conversion into highly functionalized structures such as amino sugars 51 or sphingosine derivatives. 52 For instance, the TiCl 2 (i-PrO) 2 -mediated aldol reaction of 88b with crotonaldehyde afforded a single diastereomer of the expected adduct 90 in a 78% yield (Scheme 22). Further displacement of the bromine by an azido group and stereoselective Evans-Chapman-Carreira reduction of the carbonyl group afforded the 1,3-anti diol 91, which was easily converted into the fully protected amino polyol 92.…”

Section: Short Review Syn Thesismentioning

confidence: 99%

Substrate-Controlled Aldol Reactions from Chiral α-Hydroxy Ketones

2016

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Chiral α-hydroxy ketones are valuable platforms from which highly stereoselective substrate-controlled aldol reactions may be performed. The suitable choice of the hydroxyl protecting group and the enolization conditions produce aldol adducts that can be easily manipulated to give a variety of enantiomerically pure compounds. Moreover, such aldol reactions often play a crucial role in the coupling of elaborate fragments in advanced steps of the synthesis of natural products. Together, these features confer to the α-hydroxy ketones a prominent position among the chiral substrates that are capable of providing highly asymmetric transformations. 1 Introduction 2 Pioneering Contributions 3 Boron-Mediated Aldol Reactions from α-Hydroxy Ethyl Ketones 4 Titanium-Mediated Aldol Reactions from α-Hydroxy Ethyl Ketones 5 Other Aldol Reactions from α-Hydroxy Ethyl Ketones 6 Aldol Reactions from α-Hydroxy Methyl Ketones 7 Conclusions

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“…Examples of dehalogenation (Cl, Br and I) and reductive removal of chalcogen groups (SR and SeR) are well known [ 1 , 2 , 3 , 4 , 5 ]. Scheme 2 shows some recent examples of debromination starting from bromide 1 [ 6 ], 2 [ 7 ] or 3 [ 8 ]. The most popular thermal initiator is azobisisobutyronitrile (AIBN), with a half-life of 1 h at 81 °C.…”

Section: (Tms) 3 Sih As Radical-based Reducing mentioning

confidence: 99%

Recent Applications of the (TMS)3SiH Radical-Based Reagent

Chatgilialoglu

Lalevée

2012

Molecules

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This review article focuses on the recent applications of tris(trimethylsilyl)silane as a radical-based reagent in organic chemistry. Numerous examples of the successful use of (TMS)3SiH in radical reductions, hydrosilylation and consecutive radical reactions are given. The use of (TMS)3SiH allows reactions to be carried out under mild conditions with excellent yields of products and remarkable chemo-, regio-, and stereoselectivity. The strategic role of (TMS)3SiH in polymerization is underlined with emphasis on the photo-induced radical polymerization of olefins and photo-promoted cationic polymerization of epoxides.

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Synthesis and Biological Evaluation of 1‐Deoxy‐5‐hydroxysphingosine Derivatives

Cited by 9 publications

References 41 publications

Asymmetric synthesis and cytotoxic activity of isomeric phytosphingosine derivatives

Asymmetric synthesis and cytotoxic activity of isomeric phytosphingosine derivatives

Substrate-Controlled Aldol Reactions from Chiral α-Hydroxy Ketones

Recent Applications of the (TMS)3SiH Radical-Based Reagent

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