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

The highly diastereoselective conjugate addition of lithium (S)-N-benzyl-N-(α-methylbenzyl)amide to a γ-silyloxy-α,β-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-phytosph...

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Main Authors: Abraham, E, Candela-Lena, J, Davies, S, Georgiou, M, Nicholson, R, Roberts, P, Russell, A, Sanchez-Fernandez, E, Smith, A, Thomson, J
Format: Journal article
Language:English
Published: 2007
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author Abraham, E
Candela-Lena, J
Davies, S
Georgiou, M
Nicholson, R
Roberts, P
Russell, A
Sanchez-Fernandez, E
Smith, A
Thomson, J
author_facet Abraham, E
Candela-Lena, J
Davies, S
Georgiou, M
Nicholson, R
Roberts, P
Russell, A
Sanchez-Fernandez, E
Smith, A
Thomson, J
author_sort Abraham, E
collection OXFORD
description The highly diastereoselective conjugate addition of lithium (S)-N-benzyl-N-(α-methylbenzyl)amide to a γ-silyloxy-α,β-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. © 2007 Elsevier Ltd. All rights reserved.
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spelling oxford-uuid:2c1ee0d2-9f95-4845-a819-81f2f305dd682022-03-26T12:35:03ZAsymmetric synthesis of N,O,O,O-tetra-acetyl D-lyxo-phytosphingosine, jaspine B (pachastrissamine) and its C(2)-epimerJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:2c1ee0d2-9f95-4845-a819-81f2f305dd68EnglishSymplectic Elements at Oxford2007Abraham, ECandela-Lena, JDavies, SGeorgiou, MNicholson, RRoberts, PRussell, ASanchez-Fernandez, ESmith, AThomson, JThe highly diastereoselective conjugate addition of lithium (S)-N-benzyl-N-(α-methylbenzyl)amide to a γ-silyloxy-α,β-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. © 2007 Elsevier Ltd. All rights reserved.
spellingShingle Abraham, E
Candela-Lena, J
Davies, S
Georgiou, M
Nicholson, R
Roberts, P
Russell, A
Sanchez-Fernandez, E
Smith, A
Thomson, J
Asymmetric synthesis of N,O,O,O-tetra-acetyl D-lyxo-phytosphingosine, jaspine B (pachastrissamine) and its C(2)-epimer
title Asymmetric synthesis of N,O,O,O-tetra-acetyl D-lyxo-phytosphingosine, jaspine B (pachastrissamine) and its C(2)-epimer
title_full Asymmetric synthesis of N,O,O,O-tetra-acetyl D-lyxo-phytosphingosine, jaspine B (pachastrissamine) and its C(2)-epimer
title_fullStr Asymmetric synthesis of N,O,O,O-tetra-acetyl D-lyxo-phytosphingosine, jaspine B (pachastrissamine) and its C(2)-epimer
title_full_unstemmed Asymmetric synthesis of N,O,O,O-tetra-acetyl D-lyxo-phytosphingosine, jaspine B (pachastrissamine) and its C(2)-epimer
title_short Asymmetric synthesis of N,O,O,O-tetra-acetyl D-lyxo-phytosphingosine, jaspine B (pachastrissamine) and its C(2)-epimer
title_sort asymmetric synthesis of n o o o tetra acetyl d lyxo phytosphingosine jaspine b pachastrissamine and its c 2 epimer
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