A direct organocatalytic entry to sphingoids:: asymmetric synthesis of D-arabino- and L-ribo-phytosphingosine

被引：82

作者：

Enders, D ^{[1
]}

Palecek, J ^{[1
]}

Grondal, C ^{[1
]}

机构：

[1] Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany

来源：

CHEMICAL COMMUNICATIONS | 2006年 / 06期

关键词：

D O I：

10.1039/b515007h

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The organocatalytic asymmetric synthesis of D-arabino- and L-ribo-phytosphingosine is described employing a diastereo-and enantioselective (S)-proline-catalyzed aldol reaction of 2,2-dimethyl-1,3-dioxan-5-one and pentadecanal as the key step.

引用

页码：655 / 657

页数：3

共 56 条

[21] Catalytic asymmetric syntheses of antifungal sphingofungins and their biological activity as potent inhibitors of serine palmitoyltransferase (SPT)
Kobayashi, S
Furuta, T
Hayashi, T
Nishijima, M
Hanada, K
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (05) : 908 - 919
[22] Kolter T, 1999, ANGEW CHEM INT EDIT, V38, P1532, DOI 10.1002/(SICI)1521-3773(19990601)38:11<1532::AID-ANIE1532>3.0.CO
[23] 2-U
[24] Kolter T., 2004, Highlights in Bioorganic Chemistry: Methods and Applications, P48, DOI [10.1002/3527603727.ch1d, DOI 10.1002/3527603727.CH1D]
[25] Koskinen PM, 1998, SYNTHESIS-STUTTGART, P1075
[26] HALICYLINDROSIDES, ANTIFUNGAL AND CYTOTOXIC CEREBROSIDES FROM THE MARINE SPONGE HALICHONDRIA-CYLINDRATA
LI, HY
MATSUNAGA, S
FUSETANI, N
[J]. TETRAHEDRON, 1995, 51 (08) : 2273 - 2280
[27] LI YT, 1984, J BIOL CHEM, V259, P8980
[28] Chemistry and biology of sphingolipids
Liao, JY
Tao, JH
Lin, GQ
Liu, DG
[J]. TETRAHEDRON, 2005, 61 (20) : 4715 - 4733
[29] A concise route to phytosphingosine from lyxose
Lin, CC
Fan, GT
Fang, JM
[J]. TETRAHEDRON LETTERS, 2003, 44 (28) : 5281 - 5283
[30] Proline-catalyzed direct asymmetric aldol reactions
List, B
Lerner, RA
Barbas, CF
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (10) : 2395 - 2396

← 1 2 3 4 5 6 →