Enantioselective synthesis for the antipodes of slagenins B and C: Establishment of absolute stereochemistry

被引：18

作者：

Jiang, B ^{[1
]}

Liu, JF ^{[1
]}

Zhao, SY ^{[1
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organomet Chem, Shanghai 200032, Peoples R China

来源：

ORGANIC LETTERS | 2001年 / 3卷 / 25期

关键词：

D O I：

10.1021/ol016689+

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] The total synthesis for the (-)-antipode of slagenin B (12) and the (+)-antipode of slagenin C (13) was achieved with the condensation of glyoxal hydrate 10 and urea as the key step. The absolute stereochemistries of naturally isolated slagenins B and C were assigned to be (9R,11R,15R)-1b and (9R,11S,15S)-1c, respectively.

引用

收藏

页码：4011 / 4013

页数：3

相关论文

共 15 条

[1] A CONVENIENT PREPARATION OF ACETONE SOLUTIONS OF DIMETHYLDIOXIRANE [J].

ADAM, W ;

BIALAS, J ;

HADJIARAPOGLOU, L .

CHEMISCHE BERICHTE, 1991, 124 (10) :2377-2377

[2] Reductions of 1,3-dicarbonyl systems with ruthenium-biarylbisphosphine catalysts [J].

Ager, DJ ;

Laneman, SA .

TETRAHEDRON-ASYMMETRY, 1997, 8 (20) :3327-3355

[3]

COREY EJ, 1975, TETRAHEDRON LETT, P2643

[4]

COSSY J, 1987, SYNTHESIS-STUTTGART, P1113

[5] Asymmetric synthesis of (+)-negamycin [J].

Davies, SG ;

Ichihara, O .

TETRAHEDRON-ASYMMETRY, 1996, 7 (07) :1919-1922

[6] Marine natural products [J].

Faulkner, DJ .

NATURAL PRODUCT REPORTS, 2001, 18 (01) :1-49

[7] SYNTHESIS OF UNSYMMETRICALLY SUBSTITUTED HEXAHYDROIMIDAZO [4,5-D] IMIDAZOLE-2,5-DIONES AND ELUCIDATION OF REACTION PATHWAYS [J].

GAUTAM, S ;

KETCHAM, R ;

NEMATOLLAHI, J .

SYNTHETIC COMMUNICATIONS, 1979, 9 (10) :863-870

[8] ISOLATION AND X-RAY STRUCTURE OF THE INTERMEDIATE DIHYDROXYIMIDAZOLIDINE(DHI) IN THE SYNTHESIS OF GLYCOLURIL FROM GLYOXAL AND UREA [J].

GRILLON, E ;

GALLO, R ;

PIERROT, M ;

BOILEAU, J ;

WIMMER, E .

TETRAHEDRON LETTERS, 1988, 29 (09) :1015-1016

[9] OXIDATION OF DIAZO-COMPOUNDS BY DIMETHYL DIOXIRANE - AN EXTREMELY MILD AND EFFICIENT METHOD FOR THE PREPARATION OF LABILE ALPHA-OXO-ALDEHYDES [J].

IHMELS, H ;

MAGGINI, M ;

PRATO, M ;

SCORRANO, G .

TETRAHEDRON LETTERS, 1991, 32 (43) :6215-6218

[10] STUDY OF THE ANOMERIC EFFECT IN 2-SUBSTITUTED 1,3-DITHIANES [J].

JUARISTI, E ;

TAPIA, J ;

MENDEZ, R .

TETRAHEDRON, 1986, 42 (05) :1253-1264