Stereoselective synthesis of β-amino alcohols:: practical preparation of all four stereomers of N-PMB-protected sphingosine from L- and D-serine

被引：30

作者：

Chung, SK ^{[1
]}

Lee, JM ^{[1
]}

机构：

[1] Pohang Univ Sci & Technol, Dept Chem, Pohang 790784, South Korea

来源：

TETRAHEDRON-ASYMMETRY | 1999年 / 10卷 / 08期

关键词：

D O I：

10.1016/S0957-4166(99)00147-0

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Serine was efficiently converted to the N-p-methoxybenzyl (PMB) protected alpha'-amino enone derivative 6, which was reduced with Zn(BH4)(2) to the corresponding anti-beta-amino alcohol in >96% de. On the other hand, N-PMB-N-Boc-protected alpha'-amino enone derivative 8 was reduced by NaBH4 to syn-product with a diastereoselectivity of ca. 90%. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：1441 / 1444

页数：4

共 28 条

[1] The asymmetric Horner-Emmons reaction using a benzopyrano-isoxazolidine auxiliary [J].

Abiko, A ;

Masamune, S .

TETRAHEDRON LETTERS, 1996, 37 (07) :1077-1080

[2] HORNER-WADSWORTH-EMMONS REACTION - USE OF LITHIUM-CHLORIDE AND AN AMINE FOR BASE SENSITIVE COMPOUNDS [J].

BLANCHETTE, MA ;

CHOY, W ;

DAVIS, JT ;

ESSENFELD, AP ;

MASAMUNE, S ;

ROUSH, WR ;

SAKAI, T .

TETRAHEDRON LETTERS, 1984, 25 (21) :2183-2186

[3] ASYMMETRIC SYNTHESES OF OPTICALLY-ACTIVE ALPHA,BETA-DISUBSTITUTED BETA-AMINO ACIDS [J].

BURGESS, K ;

LIU, LT ;

PAL, B .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (17) :4758-4763

[4]

CARDILLO G, 1996, CHEM SOC REV, P117

[5] Stereoselective synthesis of beta-amino alcohols: diastereoselective reduction of chiral alpha'-amino enones derived from amino acids [J].

Chung, SK ;

Kang, DN .

TETRAHEDRON-ASYMMETRY, 1997, 8 (18) :3027-3030

[6] Glycolipids from sponges.: 6.: Plakoside A and B, two unique prenylated glycosphingolipids with immunosuppressive activity from the marine sponge Plakortis simplex [J].

Costantino, V ;

Fattorusso, E ;

Mangoni, A ;

Di Rosa, M ;

Ianaro, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (51) :12465-12470

[7]

ELIEL EL, 1983, ASYMMETRIC SYNTHESIS, V2, P125

[8] DIRECTED REDUCTION OF BETA-HYDROXY KETONES EMPLOYING TETRAMETHYLAMMONIUM TRIACETOXYBOROHYDRIDE [J].

EVANS, DA ;

CHAPMAN, KT ;

CARREIRA, EM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (11) :3560-3578

[9] CARBOHYDRATE DIFFERENTIATION ANTIGENS - PROBABLE LIGANDS FOR CELL-ADHESION MOLECULES [J].

FEIZI, T .

TRENDS IN BIOCHEMICAL SCIENCES, 1991, 16 (03) :84-86

[10] A STEREODIVERGENT SYNTHESIS OF D-ERYTHRO-SPHINGOSINE AND D-THREO-SPHINGOSINE FROM L-SERINE [J].

GARNER, P ;

PARK, JM ;

MALECKI, E .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (18) :4395-4398

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