CHIRAL, CYCLIC AMINO ALDEHYDES IN THE BAYLIS-HILLMAN REACTION - A ROUTE TO SPHINGOSINE ANALOGS

被引:34
作者
DREWES, SE
KHAN, AA
ROWLAND, K
机构
[1] Department of Chemistry, University of Natal, Pietermaritzburg
关键词
D O I
10.1080/00397919308009766
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
(L)-Serine and (S)-prolinol, after suitable protection and transformations, react smoothly with methyl acrylate and DABCO (Baylis-Hillman reaction). The product from the (L)-serine reaction can be regarded as an analogue of sphingosine.
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页码:183 / 188
页数:6
相关论文
共 11 条
[1]  
DREWES MW, 1988, THESIS U MARBURG, P64
[2]   STEREOSELECTIVE SYNTHESIS OF ALPHA-METHYLENE-BETA-HYDROXY-GAMMA-ALKOXY ESTERS AND KETONES [J].
DREWES, SE ;
MANICKUM, T ;
ROOS, GHP .
SYNTHETIC COMMUNICATIONS, 1988, 18 (10) :1065-1070
[3]   FACILE DIASTEREOSELECTIVE SYNTHESIS OF 2,6-DIALKYL-5-METHYLENE-1,3-DIOXAN-4-ONES VIA ALPHA-ACTIVATED VINYL ESTERS [J].
DREWES, SE ;
EMSLIE, ND ;
KARODIA, N ;
KHAN, AA .
CHEMISCHE BERICHTE, 1990, 123 (06) :1447-1448
[4]   THE SYNTHESIS AND CONFIGURATIONAL STABILITY OF DIFFERENTIALLY PROTECTED BETA-HYDROXY-ALPHA-AMINO ALDEHYDES [J].
GARNER, P ;
PARK, JM .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (12) :2361-2364
[5]   CHIROSPECIFIC SYNTHESIS OF AMINO-ACIDS, AMINO ALDEHYDES AND AMINO-ALCOHOLS FROM D-GLUCOSAMINE HYDROCHLORIDE - A MULTIGRAM SYNTHESIS OF N-BOC-L-SERINAL [J].
GIANNIS, A ;
HENK, T .
TETRAHEDRON LETTERS, 1990, 31 (09) :1253-1256
[6]   GLYCOSPHINGOLIPIDS [J].
HAKOMORI, S .
SCIENTIFIC AMERICAN, 1986, 254 (05) :44-&
[7]  
HANNUN YA, 1987, J BIOL CHEM, V262, P13620
[8]  
KOSKINEN AMP, 1990, SYNLETT, P665
[9]  
MANICKUM T, 1990, SYNTH COMMUN, V20
[10]   A FACILE DIAGNOSTIC H-1-NMR METHOD FOR SYN AND ANTI HYDROXY SYSTEMS [J].
ROOS, GHP ;
MANICKUM, T ;
MALISSAR, DG .
JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 1992, 39 (01) :105-106