Asymmetric synthesis of vicinal amino alcohols: xestoaminol C, sphinganine and sphingosine

Elin Abraham; Stephen G. Davies; Nicholas L. Millican; Rebecca L. Nicholson; Paul M. Roberts; Andrew D. Smith

doi:10.1039/b801357h

Asymmetric synthesis of vicinal amino alcohols: xestoaminol C, sphinganine and sphingosine

Elin Abraham, Stephen G. Davies, Nicholas L. Millican, Rebecca L. Nicholson, Paul M. Roberts, Andrew D. Smith

Research output: Contribution to journal › Article › peer-review

Abstract

The highly diastereoselective anti-aminohydroxylation of alpha,beta-unsaturated esters, via conjugate addition of lithium (S)-N-benzyl-N-(alpha-methylbenzyl) amide and subsequent in situ enolate oxidation with (+)-(camphorsulfonyl) oxaziridine, has been used as the key step in the asymmetric synthesis of N,O-diacetyl xestoaminol C(41% yield over 8 steps), N,O,O- triacetyl sphinganine (30% yield over 8 steps) and N,O,O-triacetyl sphingosine (30% yield over 7 steps).

Original language	English
Pages (from-to)	1655-1664
Number of pages	10
Journal	Organic & Biomolecular Chemistry
Volume	6
Issue number	9
DOIs	https://doi.org/10.1039/b801357h
Publication status	Published - 2008

Keywords

D-ERYTHRO-SPHINGOSINE
EFFICIENT STEREOSELECTIVE-SYNTHESIS
OLEFIN CROSS-METATHESIS
D-RIBO-PHYTOSPHINGOSINE
D-LYXO-PHYTOSPHINGOSINE
IODOXYBENZOIC ACID IBX
D-THREO-SPHINGOSINE
(2S,3R)-3-AMINO-2-HYDROXYDECANOIC ACID
ENANTIOSELECTIVE SYNTHESES
STEREOSPECIFIC SYNTHESIS

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@article{ab213349efe74e788dabde94e5685e9e,

title = "Asymmetric synthesis of vicinal amino alcohols: xestoaminol C, sphinganine and sphingosine",

abstract = "The highly diastereoselective anti-aminohydroxylation of alpha,beta-unsaturated esters, via conjugate addition of lithium (S)-N-benzyl-N-(alpha-methylbenzyl) amide and subsequent in situ enolate oxidation with (+)-(camphorsulfonyl) oxaziridine, has been used as the key step in the asymmetric synthesis of N,O-diacetyl xestoaminol C(41% yield over 8 steps), N,O,O- triacetyl sphinganine (30% yield over 8 steps) and N,O,O-triacetyl sphingosine (30% yield over 7 steps).",

keywords = "D-ERYTHRO-SPHINGOSINE, EFFICIENT STEREOSELECTIVE-SYNTHESIS, OLEFIN CROSS-METATHESIS, D-RIBO-PHYTOSPHINGOSINE, D-LYXO-PHYTOSPHINGOSINE, IODOXYBENZOIC ACID IBX, D-THREO-SPHINGOSINE, (2S,3R)-3-AMINO-2-HYDROXYDECANOIC ACID, ENANTIOSELECTIVE SYNTHESES, STEREOSPECIFIC SYNTHESIS",

author = "Elin Abraham and Davies, {Stephen G.} and Millican, {Nicholas L.} and Nicholson, {Rebecca L.} and Roberts, {Paul M.} and Smith, {Andrew D.}",

year = "2008",

doi = "10.1039/b801357h",

language = "English",

volume = "6",

pages = "1655--1664",

journal = "Organic & Biomolecular Chemistry",

issn = "1477-0539",

publisher = "Royal Society of Chemistry",

number = "9",

}

TY - JOUR

T1 - Asymmetric synthesis of vicinal amino alcohols: xestoaminol C, sphinganine and sphingosine

AU - Abraham, Elin

AU - Davies, Stephen G.

AU - Millican, Nicholas L.

AU - Nicholson, Rebecca L.

AU - Roberts, Paul M.

AU - Smith, Andrew D.

PY - 2008

Y1 - 2008

N2 - The highly diastereoselective anti-aminohydroxylation of alpha,beta-unsaturated esters, via conjugate addition of lithium (S)-N-benzyl-N-(alpha-methylbenzyl) amide and subsequent in situ enolate oxidation with (+)-(camphorsulfonyl) oxaziridine, has been used as the key step in the asymmetric synthesis of N,O-diacetyl xestoaminol C(41% yield over 8 steps), N,O,O- triacetyl sphinganine (30% yield over 8 steps) and N,O,O-triacetyl sphingosine (30% yield over 7 steps).

AB - The highly diastereoselective anti-aminohydroxylation of alpha,beta-unsaturated esters, via conjugate addition of lithium (S)-N-benzyl-N-(alpha-methylbenzyl) amide and subsequent in situ enolate oxidation with (+)-(camphorsulfonyl) oxaziridine, has been used as the key step in the asymmetric synthesis of N,O-diacetyl xestoaminol C(41% yield over 8 steps), N,O,O- triacetyl sphinganine (30% yield over 8 steps) and N,O,O-triacetyl sphingosine (30% yield over 7 steps).

KW - D-ERYTHRO-SPHINGOSINE

KW - EFFICIENT STEREOSELECTIVE-SYNTHESIS

KW - OLEFIN CROSS-METATHESIS

KW - D-RIBO-PHYTOSPHINGOSINE

KW - D-LYXO-PHYTOSPHINGOSINE

KW - IODOXYBENZOIC ACID IBX

KW - D-THREO-SPHINGOSINE

KW - (2S,3R)-3-AMINO-2-HYDROXYDECANOIC ACID

KW - ENANTIOSELECTIVE SYNTHESES

KW - STEREOSPECIFIC SYNTHESIS

U2 - 10.1039/b801357h

DO - 10.1039/b801357h

M3 - Article

SN - 1477-0539

VL - 6

SP - 1655

EP - 1664

JO - Organic & Biomolecular Chemistry

JF - Organic & Biomolecular Chemistry

IS - 9

ER -

Asymmetric synthesis of vicinal amino alcohols: xestoaminol C, sphinganine and sphingosine

Abstract

Keywords

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