Asymmetric synthesis of N,O,O,O-tetra-acetyl D-lyxo-phytosphingosine, jaspine B (pachastrissamine), 2-epi-jaspine B, and deoxoprosophylline via lithium amide conjugate addition

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

doi:10.1039/b801671b

Asymmetric synthesis of N,O,O,O-tetra-acetyl D-lyxo-phytosphingosine, jaspine B (pachastrissamine), 2-epi-jaspine B, and deoxoprosophylline via lithium amide conjugate addition

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

Research output: Contribution to journal › Review article › peer-review

Abstract

The highly diastereoselective anti-aminohydroxylation of (E)-gamma-tri-iso-propylsilyloxy-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,O,O-tetra-acetyl D-lyxo-phytosphingosine (20% yield over 7 steps), the anhydrophytosphingosine jaspine B (10% yield over 9 steps), 2-epi-jaspine B (14% yield over 9 steps), and the Prosopis alkaloid deoxoprosophylline (26% yield over 7 steps).

Original language	English
Pages (from-to)	1665-1673
Number of pages	9
Journal	Organic & Biomolecular Chemistry
Volume	6
Issue number	9
DOIs	https://doi.org/10.1039/b801671b
Publication status	Published - 2008

Keywords

D-RIBO-PHYTOSPHINGOSINE
STEREOSELECTIVE TOTAL-SYNTHESIS
D-ERYTHRO-SPHINGOSINE
ENANTIOSELECTIVE TOTAL-SYNTHESIS
INTRAMOLECULAR N-ALKYLATION
PIPERIDINE RING FORMATION
CHIRAL BUILDING-BLOCK
CYTOTOXIC ANHYDROPHYTOSPHINGOSINE
EFFICIENT SYNTHESIS
FORMAL SYNTHESIS

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Abraham, E., Brock, E. A., Candela-Lena, J. I., Davies, S. G., Georgiou, M., Nicholson, R. L., Perkins, J. H., Roberts, P. M., Russell, A. J., Sanchez-Fernandez, E. M., Scott, P. M., Smith, A. D., & Thomson, J. E. (2008). Asymmetric synthesis of N,O,O,O-tetra-acetyl D-lyxo-phytosphingosine, jaspine B (pachastrissamine), 2-epi-jaspine B, and deoxoprosophylline via lithium amide conjugate addition. Organic & Biomolecular Chemistry, 6(9), 1665-1673. https://doi.org/10.1039/b801671b

@article{7f02becca0eb44a3a8c7c407da4613ba,

title = "Asymmetric synthesis of N,O,O,O-tetra-acetyl D-lyxo-phytosphingosine, jaspine B (pachastrissamine), 2-epi-jaspine B, and deoxoprosophylline via lithium amide conjugate addition",

abstract = "The highly diastereoselective anti-aminohydroxylation of (E)-gamma-tri-iso-propylsilyloxy-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,O,O-tetra-acetyl D-lyxo-phytosphingosine (20% yield over 7 steps), the anhydrophytosphingosine jaspine B (10% yield over 9 steps), 2-epi-jaspine B (14% yield over 9 steps), and the Prosopis alkaloid deoxoprosophylline (26% yield over 7 steps).",

keywords = "D-RIBO-PHYTOSPHINGOSINE, STEREOSELECTIVE TOTAL-SYNTHESIS, D-ERYTHRO-SPHINGOSINE, ENANTIOSELECTIVE TOTAL-SYNTHESIS, INTRAMOLECULAR N-ALKYLATION, PIPERIDINE RING FORMATION, CHIRAL BUILDING-BLOCK, CYTOTOXIC ANHYDROPHYTOSPHINGOSINE, EFFICIENT SYNTHESIS, FORMAL SYNTHESIS",

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

year = "2008",

doi = "10.1039/b801671b",

language = "English",

volume = "6",

pages = "1665--1673",

journal = "Organic & Biomolecular Chemistry",

issn = "1477-0539",

publisher = "Royal Society of Chemistry",

number = "9",

}

Abraham, E, Brock, EA, Candela-Lena, JI, Davies, SG, Georgiou, M, Nicholson, RL, Perkins, JH, Roberts, PM, Russell, AJ, Sanchez-Fernandez, EM, Scott, PM, Smith, AD & Thomson, JE 2008, 'Asymmetric synthesis of N,O,O,O-tetra-acetyl D-lyxo-phytosphingosine, jaspine B (pachastrissamine), 2-epi-jaspine B, and deoxoprosophylline via lithium amide conjugate addition', Organic & Biomolecular Chemistry, vol. 6, no. 9, pp. 1665-1673. https://doi.org/10.1039/b801671b

Asymmetric synthesis of N,O,O,O-tetra-acetyl D-lyxo-phytosphingosine, jaspine B (pachastrissamine), 2-epi-jaspine B, and deoxoprosophylline via lithium amide conjugate addition. / Abraham, Elin; Brock, E. Anne; Candela-Lena, Jose I. et al.
In: Organic & Biomolecular Chemistry, Vol. 6, No. 9, 2008, p. 1665-1673.

Research output: Contribution to journal › Review article › peer-review

TY - JOUR

T1 - Asymmetric synthesis of N,O,O,O-tetra-acetyl D-lyxo-phytosphingosine, jaspine B (pachastrissamine), 2-epi-jaspine B, and deoxoprosophylline via lithium amide conjugate addition

AU - Abraham, Elin

AU - Brock, E. Anne

AU - Candela-Lena, Jose I.

AU - Davies, Stephen G.

AU - Georgiou, Matthew

AU - Nicholson, Rebecca L.

AU - Perkins, James H.

AU - Roberts, Paul M.

AU - Russell, Angela J.

AU - Sanchez-Fernandez, Elena M.

AU - Scott, Philip M.

AU - Smith, Andrew D.

AU - Thomson, James E.

PY - 2008

Y1 - 2008

N2 - The highly diastereoselective anti-aminohydroxylation of (E)-gamma-tri-iso-propylsilyloxy-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,O,O-tetra-acetyl D-lyxo-phytosphingosine (20% yield over 7 steps), the anhydrophytosphingosine jaspine B (10% yield over 9 steps), 2-epi-jaspine B (14% yield over 9 steps), and the Prosopis alkaloid deoxoprosophylline (26% yield over 7 steps).

AB - The highly diastereoselective anti-aminohydroxylation of (E)-gamma-tri-iso-propylsilyloxy-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,O,O-tetra-acetyl D-lyxo-phytosphingosine (20% yield over 7 steps), the anhydrophytosphingosine jaspine B (10% yield over 9 steps), 2-epi-jaspine B (14% yield over 9 steps), and the Prosopis alkaloid deoxoprosophylline (26% yield over 7 steps).

KW - D-RIBO-PHYTOSPHINGOSINE

KW - STEREOSELECTIVE TOTAL-SYNTHESIS

KW - D-ERYTHRO-SPHINGOSINE

KW - ENANTIOSELECTIVE TOTAL-SYNTHESIS

KW - INTRAMOLECULAR N-ALKYLATION

KW - PIPERIDINE RING FORMATION

KW - CHIRAL BUILDING-BLOCK

KW - CYTOTOXIC ANHYDROPHYTOSPHINGOSINE

KW - EFFICIENT SYNTHESIS

KW - FORMAL SYNTHESIS

U2 - 10.1039/b801671b

DO - 10.1039/b801671b

M3 - Review article

SN - 1477-0539

VL - 6

SP - 1665

EP - 1673

JO - Organic & Biomolecular Chemistry

JF - Organic & Biomolecular Chemistry

IS - 9

ER -

Asymmetric synthesis of N,O,O,O-tetra-acetyl D-lyxo-phytosphingosine, jaspine B (pachastrissamine), 2-epi-jaspine B, and deoxoprosophylline via lithium amide conjugate addition

Abstract

Keywords

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