Stereodivergent and regioselective synthesis of 3,4-cis- and 3,4-trans-pyrrolidinediols from α-amino acids

被引:19
作者
Kim, JH
Long, MJC
Kim, JY
Park, KH [1 ]
机构
[1] Gyeongsang Natl Univ, Div Appl Life Sci, Program Bk21, Dept Agr Chem, Jinju, South Korea
[2] Univ Oxford, Chem Res Lab, Oxford OX1 3TA, England
关键词
D O I
10.1021/ol049237g
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] Highly stereodivergent Woodward-Prevost reaction applied to iodoacetates derived from homochiral alpha-amino acids afforded enantiopure 3,4-cis- and 3,4-trans-pyrrolidinediol derivatives, with control over the protecting group, allowing for differential protection.
引用
收藏
页码:2273 / 2276
页数:4
相关论文
共 35 条
[1]   Woodward-Prevost reactions of 1,7-dioxaspiro[5.5]undec-4-enes [J].
Brimble, MA ;
Nairn, MR .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (14) :4801-4805
[2]   SPECTROSCOPIC INVESTIGATION OF SWAINSONINE - ALPHA-MANNOSIDASE INHIBITOR ISOLATED FROM SWAINSONA-CANESCENS [J].
COLEGATE, SM ;
DORLING, PR ;
HUXTABLE, CR .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1979, 32 (10) :2257-2264
[3]   Formal total synthesis of enantiopure (-)-anisomycin, antibiotic from Streptomyces [J].
Delair, P ;
Brot, E ;
Kanazawa, A ;
Greene, AE .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (04) :1383-1386
[4]  
ELBEIN AD, 1987, ANNU REV BIOCHEM, V56, P496
[5]   SYNTHESIS OF HOMOCHIRAL BETA-HYDROXY-ALPHA-AMINO-ACIDS [(2S,3R,4R)-3,4-DIHYDROXYPROLINE AND (2S,3R,4R)-3,4-DIHYDROXYPIPECOLIC ACID] AND OF 1,4-DIDEOXY-1,4-IMINO-D-ARABINITOL [DAB1] AND FAGOMINE [1,5-IMINO-1,2,5-TRIDEOXY-D-ARABINO-HEXITOL] [J].
FLEET, GWJ ;
WITTY, DR .
TETRAHEDRON-ASYMMETRY, 1990, 1 (02) :119-136
[6]   ISOLATION AND CHARACTERIZATION OF A 1-PYRIDINE FUNGAL ALKALOID [J].
GUENGERICH, FP ;
DIMARI, SJ ;
BROQUIST, HP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (06) :2055-2056
[7]   Submission of some iodoformates to the Woodward-Prevost conditions [J].
Hamm, S ;
Hennig, L ;
Findeisen, M ;
Müller, D ;
Welzel, P .
TETRAHEDRON, 2000, 56 (10) :1345-1348
[8]   The efficient, enantioselective synthesis of aza sugars from amino acids .1. The polyhydroxylated pyrrolidines [J].
Huang, YF ;
Dalton, DR ;
Carroll, PJ .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (02) :372-376
[9]   An aldol-based approach to the synthesis of the antibiotic Anisomycin [J].
Hulme, AN ;
Rosser, EM .
ORGANIC LETTERS, 2002, 4 (02) :265-267
[10]   3-O-ALPHA-L-RHAMNOPYRANOSYL-D-GLUCOSE, A NEW DISACCHARIDE SYNTHESIZED BY KOENIGS-KNORR REACTION [J].
IMPERATO, F .
JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (21) :3478-3479