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

被引：102

作者：

Abraham, Elin ^{[1
]}

Brock, E. Anne ^{[1
]}

Candela-Lena, Jose I. ^{[1
]}

Davies, Stephen G. ^{[1
]}

Georgiou, Matthew ^{[1
]}

Nicholson, Rebecca L. ^{[1
]}

Perkins, James H. ^{[1
]}

Roberts, Paul M. ^{[1
]}

Russell, Angela J. ^{[1
]}

Sanchez-Fernandez, Elena M. ^{[1
]}

Scott, Philip M. ^{[1
]}

Smith, Andrew D. ^{[1
]}

Thomson, James E. ^{[1
]}

机构：

[1] Univ Oxford, Dept Chem, Chem Res Lab, Oxford OX1 3TA, England

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2008年 / 6卷 / 09期

关键词：

D O I：

10.1039/b801671b

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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).

引用

页码：1665 / 1673

页数：9

共 10 条

[1] 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 (vol 6, pg 1665, 2008)
Abraham, Elin
Brock, E. Anne
Candela-Lena, Jose I.
Davies, Stephen G.
Georgiou, Matthew
Nicholson, Rebecca L.
Perkins, James H.
Roberts, Paul M.
Russell, Angela J.
Sanchez-Fernandez, Elena M.
Scott, Philip M.
Smith, Andrew D.
Thomson, James E.
ORGANIC & BIOMOLECULAR CHEMISTRY, 2008, 6 (24) : 4668 - 4668
[2] Asymmetric synthesis of N,O,O,O-tetra-acetyl D-lyxo-phytosphingosine, jaspine B (pachastrissamine) and its C(2)-epimer
Abraham, Elin
Candela-Lena, Jose I.
Davies, Stephen G.
Georgiou, Matthew
Nicholson, Rebecca L.
Roberts, Paul M.
Russell, Angela J.
Sanchez-Fernandez, Elena M.
Smith, Andrew D.
Thomson, James E.
TETRAHEDRON-ASYMMETRY, 2007, 18 (21) : 2510 - 2513
[3] A common strategy for the stereoselective synthesis of anhydrophytosphingosine pachastrissamine (jaspine B) and N,O,O,O-tetra-acetyl D-lyxo-phytosphingosine
Rao, G. Srinivas
Rao, B. Venkateswara
TETRAHEDRON LETTERS, 2011, 52 (46) : 6076 - 6079
[4] A common and stereoselective strategy for the synthesis of N,O,O,O-tetra-acetyl D-ribo-(2S,3S,4R)-phytosphingosine and 2-epi-jaspine B
Rao, G. Srinivas
Rao, B. Venkateswara
TETRAHEDRON LETTERS, 2011, 52 (38) : 4861 - 4864
[5] Stereoselective synthesis of 2-epi-jaspine B via base-catalyzed intramolecular oxy-Michael conjugate addition approach
Reddipalli, Gowrisankar
Venkataiah, Mallam
Mishra, Mithilesh Kumar
Fadnavis, Nitin W.
TETRAHEDRON-ASYMMETRY, 2009, 20 (15) : 1802 - 1805
[6] Asymmetric total synthesis of sperabillins B and D via lithium amide conjugate addition
Davies, SG
Haggitt, JR
Ichihara, O
Kelly, RJ
Leech, MA
Mortimer, AJP
Roberts, PM
Smith, AD
ORGANIC & BIOMOLECULAR CHEMISTRY, 2004, 2 (18) : 2630 - 2649
[7] An expedient route for the practical synthesis of pachastrissamine (jaspine B) starting from 3,4,6-tri-O-benzyl-D-galactal
Reddy, L. Vijaya Raghava
Reddy, P. Venkat
Shaw, Arun K.
TETRAHEDRON-ASYMMETRY, 2007, 18 (04) : 542 - 546
[8] Synthesis of N-(2-hydroxy-3-methoxybenzylidene) - 2, 3, 4, 6-tetra-O-acetyl -beta-D galactopyranosylamine as a new chiral Schiff base for asymmetric [2+2] cycloadditions
Jarrahpour, A. A.
Alvand, P.
Arab, R.
Beheshti, A.
MOLBANK, 2005, (04)
[9] Stereoselective synthesis of O-tosyl azabicyclic derivatives via aza Prins reaction of endocyclic N-acyliminium ions: application to the total synthesis of (±)-epi-indolizidine 167B and 209D
Saikia, Anil K.
Indukuri, Kiran
Das, Jagadish
ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (36) : 7026 - 7035
[10] REACTION OF 6-ACETILAMINO-5-(N,B,D-2',3',4',6'-TETRA-O-ACETYL-GLUCOPYRANOSYL) ACETYLAMINO-1,3-DIMETHYL-URACYL WITH P2S5
GOMEZ, RR
DIAZ, RR
ANALES DE QUIMICA SERIE C-QUIMICA ORGANICA Y BIOQUIMICA, 1983, 79 (02): : 132 - 135

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