SYNTHESIS OF A 2-HYDROXYMETHYL-DIHYDROPYRIDONE-SYSTEM AS A FLEXIBLE BUILDING-BLOCK FOR THE PREPARATION OF AZASUGARS

被引:30
作者
ALTENBACH, HJ
WISCHNAT, R
机构
关键词
D O I
10.1016/0040-4039(95)00957-E
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
mCPBA induced oxidative cyclization of the aminoalcohol 1a under complete stereocontrol, generating after acetal formation a new diastereomerically pure key intermediate 2b for the flexible synthesis of azasugars. 2b could be converted to protected rac-mannonojirimycin 3 in only three steps.
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页码:4983 / 4984
页数:2
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共 12 条
[1]   STEREOSELECTIVE TOTAL SYNTHESIS OF METHYL ALPHA-D-GLUCOPYRANOSIDES AND ALPHA-L-GLUCOPYRANOSIDES [J].
ACHMATOWICZ, O ;
BIELSKI, R .
CARBOHYDRATE RESEARCH, 1977, 55 (MAY) :165-176
[2]  
ACHMATOWICZ O, 1981, ORGANIC SYNTHESIS TO, P307
[3]  
ALTENBACH HJ, 1995, IN PRESS TETRAHEDRON
[4]   THE CHEMISTRY OF HEXENULOSES [J].
HOLDER, NL .
CHEMICAL REVIEWS, 1982, 82 (03) :287-332
[5]  
HUGHES AB, 1994, NAT PROD REP, P135
[6]   CERIUM(IV), AS A SELECTIVE AND EFFICIENT CATALYST FOR ALCOHOLYSES OF ALLYLIC AND TERTIARY BENZYLIC ALCOHOLS [J].
IRANPOOR, N ;
MOTHAGHINEGHAD, E .
TETRAHEDRON, 1994, 50 (06) :1859-1870
[7]  
LICHTENTHALER FW, 1992, MODERN SYNTHETIC MET
[8]   REDUCTION OF NATURAL ENONES IN PRESENCE OF CERIUM TRICHLORIDE [J].
LUCHE, JL ;
RODRIGUEZHAHN, L ;
CRABBE, P .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1978, (14) :601-602
[9]  
ONABE K, 1978, J ANTIBIOT, V31, P555
[10]  
SHING TKM, 1994, ANGEW CHEM INT EDIT, V33, P2312, DOI 10.1002/anie.199423121