(2R, 3R, 5S)-5-CARBOXALDEHYDE-2,3-DIPHENYL-1,4-DIOXANE AND (2R, 3R, 5R)-5-CARBOXALDEHYDE-2,3-DIPHENYL-1,4-DIOXANE AS SURROGATES FOR OPTICALLY PURE 2,3-O-ISOPROPYLIDENEGLYCERALDEHYDE IN ASYMMETRIC-SYNTHESIS

被引:16
作者
AUBE, J
MOSSMAN, CJ
DICKEY, S
机构
[1] Department of Medicinal Chemistry University of Kansas, Lawrence
关键词
D O I
10.1016/S0040-4020(01)92276-8
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The title compounds were prepared from threo-hydrobenzoin, either enantiomer of which is readily available from trans-stilbene using the Sharpless asymmetric dihydroxylation reaction. Several organometallic reagents were added to the aldehydes and the resulting adducts treated with H-2-Pd/C to give diastereomerically and enantiomerically enriched 1,2,3-triol-containing building blocks for asymmetric synthesis.
引用
收藏
页码:9819 / 9826
页数:8
相关论文
共 35 条
[1]   ASCENT OF THE ALDOSE SERIES BY 4 CARBON-ATOMS - TOTAL SYNTHESIS OF D-GLYCERO-D-TALO-L-TALO-UNDECOSE PENTAACETONIDE [J].
CASIRAGHI, G ;
COLOMBO, L ;
RASSU, G ;
SPANU, P .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (06) :2135-2139
[2]   THE 4-CARBON ELONGATION OF 3-CARBON CHIRAL SYNTHONS USING 2-(TRIMETHYLSILOXY)FURAN - HIGHLY STEREOCONTROLLED ENTRY TO ENANTIOMERICALLY PURE 7-CARBON ALPHA,BETA-UNSATURATED 2,3-DIDEOXY-ALDONOLACTONES [J].
CASIRAGHI, G ;
COLOMBO, L ;
RASSU, G ;
SPANU, P ;
FAVA, GG ;
BELICCHI, MF .
TETRAHEDRON, 1990, 46 (16) :5807-5824
[3]   ON THE COMMUNICATION OF CHIRALITY FROM FURANOSE AND PYRANOSE RINGS TO MONOSACCHARIDE SIDE-CHAINS - ANOMALOUS RESULTS IN THE GLUCOSE SERIES [J].
DANISHEFSKY, SJ ;
DENINNO, MP ;
PHILLIPS, GB ;
ZELLE, RE ;
LARTEY, PA .
TETRAHEDRON, 1986, 42 (11) :2809-2819
[4]   REGIOSELECTIVE MANIPULATION OF HYDROXYL-GROUPS VIA ORGANOTIN DERIVATIVES [J].
DAVID, S ;
HANESSIAN, S .
TETRAHEDRON, 1985, 41 (04) :643-663
[5]   SYNTHESIS OF (-)-2S,3S,11S,12R-2,3,11,12-TETRAPHENYL[18]CROWN-6 [J].
DIETL, F ;
HAUNSCHILD, J ;
MERZ, A .
TETRAHEDRON, 1985, 41 (07) :1193-1197
[6]   REACTION OF ALDEHYDES WITH STABILIZED SULFUR YLIDES - HIGHLY STEREOSELECTIVE SYNTHESIS OF 2,3-EPOXY-AMIDES [J].
FERNANDEZ, MV ;
DURANTELANES, P ;
LOPEZHERRERA, FJ .
TETRAHEDRON, 1990, 46 (23) :7911-7922
[7]   A CONVENIENT SYNTHESIS OF (2R)-1-AMINO-1-DEOXY-1-PHOSPHINYLGLYCEROLS [J].
HANAYA, T ;
MIYOSHI, A ;
NOGUCHI, A ;
KAWAMOTO, H ;
ARMOUR, MA ;
HOGG, AM ;
YAMAMOTO, H .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1990, 63 (12) :3590-3594
[8]   THE SYNTHETIC METHODOLOGY OF NONRACEMIC GLYCIDOL AND RELATED 2,3-EPOXY ALCOHOLS [J].
HANSON, RM .
CHEMICAL REVIEWS, 1991, 91 (04) :437-475
[9]   PREPARATION AND STORAGE OF (R)-2,3-O-ISOPROPYLIDENEGLYCERALDEHYDE (D-GLYCERALDEHYDE ACETONIDE) [J].
HERTEL, LW ;
GROSSMAN, CS ;
KROIN, JS .
SYNTHETIC COMMUNICATIONS, 1991, 21 (02) :151-154
[10]   ASYMMETRIC DIHYDROXYLATION VIA LIGAND-ACCELERATED CATALYSIS [J].
JACOBSEN, EN ;
MARKO, I ;
MUNGALL, WS ;
SCHRODER, G ;
SHARPLESS, KB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (06) :1968-1970