Asymmetric synthesis of N,O,O,O-tetra-acetyl D-lyxo-phytosphingosine, jaspine B (pachastrissamine) and its C(2)-epimer

Elin Abraham; Jose I. Candela-Lena; Stephen G. Davies; Matthew Georgiou; Rebecca L. Nicholson; Paul M. Roberts; Angela J. Russell; Elena M. Sanchez-Fernandez; Andrew D. Smith; James E. Thomson

doi:10.1016/j.tetasy.2007.10.026

Asymmetric synthesis of N,O,O,O-tetra-acetyl D-lyxo-phytosphingosine, jaspine B (pachastrissamine) and its C(2)-epimer

Elin Abraham, Jose I. Candela-Lena, Stephen G. Davies, Matthew Georgiou, Rebecca L. Nicholson, Paul M. Roberts, Angela J. Russell, Elena M. Sanchez-Fernandez, Andrew D. Smith, James E. Thomson

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

Abstract

The highly diastereoselective conjugate addition of lithium (S)-N-benzyl-N-(alpha-methylbenzyl)amide to a gamma-silyloxy-alpha,beta-unsaturated ester and in situ enolate oxidation with (+)-(camphorsulfonyl)oxaziridine has been used as the key step in the asymmetric synthesis of N,O,O,O-tetra-acetyl D-lyxo-phytosphingosine, jaspine B (pachastrissamine) and its C(2)-epimer. (c) 2007 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	2510-2513
Number of pages	4
Journal	Tetrahedron: Asymmetry
Volume	18
Issue number	21
DOIs	https://doi.org/10.1016/j.tetasy.2007.10.026
Publication status	Published - 22 Oct 2007

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This output contributes to the following UN Sustainable Development Goals (SDGs)

SDG 14 Life Below Water

Keywords

IODOXYBENZOIC ACID IBX
CYTOTOXIC ANHYDROPHYTOSPHINGOSINE
STEREOSELECTIVE-SYNTHESIS
(2S,3R)-3-AMINO-2-HYDROXYDECANOIC ACID
CHEMICAL-SHIFTS
MARINE SPONGE
D-XYLOSE
DERIVATIVES
ALCOHOLS
CONFIGURATION

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10.1016/j.tetasy.2007.10.026

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Abraham, E., Candela-Lena, J. I., Davies, S. G., Georgiou, M., Nicholson, R. L., Roberts, P. M., Russell, A. J., Sanchez-Fernandez, E. M., Smith, A. D., & Thomson, J. E. (2007). Asymmetric synthesis of N,O,O,O-tetra-acetyl D-lyxo-phytosphingosine, jaspine B (pachastrissamine) and its C(2)-epimer. Tetrahedron: Asymmetry, 18(21), 2510-2513. https://doi.org/10.1016/j.tetasy.2007.10.026

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title = "Asymmetric synthesis of N,O,O,O-tetra-acetyl D-lyxo-phytosphingosine, jaspine B (pachastrissamine) and its C(2)-epimer",

abstract = "The highly diastereoselective conjugate addition of lithium (S)-N-benzyl-N-(alpha-methylbenzyl)amide to a gamma-silyloxy-alpha,beta-unsaturated ester and in situ enolate oxidation with (+)-(camphorsulfonyl)oxaziridine has been used as the key step in the asymmetric synthesis of N,O,O,O-tetra-acetyl D-lyxo-phytosphingosine, jaspine B (pachastrissamine) and its C(2)-epimer. (c) 2007 Elsevier Ltd. All rights reserved.",

keywords = "IODOXYBENZOIC ACID IBX, CYTOTOXIC ANHYDROPHYTOSPHINGOSINE, STEREOSELECTIVE-SYNTHESIS, (2S,3R)-3-AMINO-2-HYDROXYDECANOIC ACID, CHEMICAL-SHIFTS, MARINE SPONGE, D-XYLOSE, DERIVATIVES, ALCOHOLS, CONFIGURATION",

author = "Elin Abraham and Candela-Lena, \{Jose I.\} and Davies, \{Stephen G.\} and Matthew Georgiou and Nicholson, \{Rebecca L.\} and Roberts, \{Paul M.\} and Russell, \{Angela J.\} and Sanchez-Fernandez, \{Elena M.\} and Smith, \{Andrew D.\} and Thomson, \{James E.\}",

year = "2007",

month = oct,

day = "22",

doi = "10.1016/j.tetasy.2007.10.026",

language = "English",

volume = "18",

pages = "2510--2513",

journal = "Tetrahedron: Asymmetry",

issn = "0957-4166",

publisher = "Elsevier",

number = "21",

}

Abraham, E, Candela-Lena, JI, Davies, SG, Georgiou, M, Nicholson, RL, Roberts, PM, Russell, AJ, Sanchez-Fernandez, EM, Smith, AD & Thomson, JE 2007, 'Asymmetric synthesis of N,O,O,O-tetra-acetyl D-lyxo-phytosphingosine, jaspine B (pachastrissamine) and its C(2)-epimer', Tetrahedron: Asymmetry, vol. 18, no. 21, pp. 2510-2513. https://doi.org/10.1016/j.tetasy.2007.10.026

TY - JOUR

T1 - Asymmetric synthesis of N,O,O,O-tetra-acetyl D-lyxo-phytosphingosine, jaspine B (pachastrissamine) and its C(2)-epimer

AU - Abraham, Elin

AU - Candela-Lena, Jose I.

AU - Davies, Stephen G.

AU - Georgiou, Matthew

AU - Nicholson, Rebecca L.

AU - Roberts, Paul M.

AU - Russell, Angela J.

AU - Sanchez-Fernandez, Elena M.

AU - Smith, Andrew D.

AU - Thomson, James E.

PY - 2007/10/22

Y1 - 2007/10/22

N2 - The highly diastereoselective conjugate addition of lithium (S)-N-benzyl-N-(alpha-methylbenzyl)amide to a gamma-silyloxy-alpha,beta-unsaturated ester and in situ enolate oxidation with (+)-(camphorsulfonyl)oxaziridine has been used as the key step in the asymmetric synthesis of N,O,O,O-tetra-acetyl D-lyxo-phytosphingosine, jaspine B (pachastrissamine) and its C(2)-epimer. (c) 2007 Elsevier Ltd. All rights reserved.

AB - The highly diastereoselective conjugate addition of lithium (S)-N-benzyl-N-(alpha-methylbenzyl)amide to a gamma-silyloxy-alpha,beta-unsaturated ester and in situ enolate oxidation with (+)-(camphorsulfonyl)oxaziridine has been used as the key step in the asymmetric synthesis of N,O,O,O-tetra-acetyl D-lyxo-phytosphingosine, jaspine B (pachastrissamine) and its C(2)-epimer. (c) 2007 Elsevier Ltd. All rights reserved.

KW - IODOXYBENZOIC ACID IBX

KW - CYTOTOXIC ANHYDROPHYTOSPHINGOSINE

KW - STEREOSELECTIVE-SYNTHESIS

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

KW - CHEMICAL-SHIFTS

KW - MARINE SPONGE

KW - D-XYLOSE

KW - DERIVATIVES

KW - ALCOHOLS

KW - CONFIGURATION

UR - https://www.scopus.com/pages/publications/36148970785

U2 - 10.1016/j.tetasy.2007.10.026

DO - 10.1016/j.tetasy.2007.10.026

M3 - Article

SN - 0957-4166

VL - 18

SP - 2510

EP - 2513

JO - Tetrahedron: Asymmetry

JF - Tetrahedron: Asymmetry

IS - 21

ER -

Asymmetric synthesis of N,O,O,O-tetra-acetyl D-lyxo-phytosphingosine, jaspine B (pachastrissamine) and its C(2)-epimer

Abstract

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Keywords

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